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How Many Times Do I Have To Repeat The Same Thing – Real Estate Investing Problems

This saga doesn’t end! Just when you think I will get the final answer from the HOA and be able to know why they think they have the authority to do what they are doing, I get nothing. No response to the questions I have. No validation on why they think they can do what they are doing. Nothing. This is continuing to heat up. The funny thing is this. They think they can just kick the can down the road and I am just going to go away. Nope. Not in my blood. This is a real estate investment property for me. I have no plans of going away any time soon. So here we go! Let the saga continue!

Get caught up on everything that has happened to this point! This has been a wild journey to say the least and it is definitely not over! Below are the links to all the craziness in this saga!

Over 24 Hours Later…Following Up Again

The fact I have to continue following up with this HOA is very frustrating. I have to ask more specific questions and be extremely clear just so I can get the response to what I want them to specifically answer. If I don’t, I end up having to wait 48 hours for a response.

So time for another follow-up email to the HOA:

Following up on this email again as I have yet to hear a response and called this morning with no response back after I was told I would receive a call back shortly. I would like to rent my place long term.

Renter information:
Father, mother and 12 year old son.
Duration of lease:
6 months
Information about tenants:
Snowbirds who have been in Orlando for over 3 months and don’t plan to currently go back to their home due to COVID-19 outbreak in tristate area.
Questions below:
  • What other information would I need to provide for approval?
  • They would like to move in ASAP. Once approved, when would the earliest they can move in be?
Thanks for your time, I look forward to hearing from you soon regarding this important and very time sensitive matter. 
I have now given the HOA everything they could possibly need to approve or reject these guests from coming. Now time to wait, even longer, to get a response.
Time To Really Laugh At Their Response
Before I just demolish this response below, let’s be fair. This HOA/Board, I am sure, thinks they are doing the right thing. I would be amazed if they actually thought they weren’t doing the right thing. This response below is just comical at this point though.

Good Afternoon,

Firstly, the Governor of Florida late last night extended the ban on new vacation rentals with EO 20-103. This ban is now through the end of April.

We not too long ago issued a notice.

Regarding the rental request for 6 months. Normally, the information below would be enough for a decision. But with the ban now extended we will deny entry to all new guests.

I will send over your request to the board.

Again, continuing to have a common theme here. No answers to the questions I have asked. Or continuing to defer the answer to these questions. Really really disappointing to see, but I am honestly not surprised based off everything that has been going on.

Now time to wait again.

2 Hours Later, Here Is There Pathetic Response

Two hours later, they finally get back with an actual response. And boy is it pathetic.

Hi YRB33,

I sent over your request below to the board for approval. Unfortunately, the board has denied your request below.

Thanks and stay safe.

Again, not surprising. No reasoning on why they are denying my request. Just stating the request has been denied and nothing more.

I continue to want them to dig an even bigger rabbit hole for themselves. For that reason, I am not done continuing to follow up with them via email. Documented communication is the best for of communication for fighting things in the future.

My Response, Simple Yet Effective

Now time for my response. Keeping it simple and effective:

Can I please have an explanation from the board as to specifically why the request is being denied?

I didn’t want to overcomplicate things for them. They have clearly shown they don’t handle communication well.

Here is why I asked the question I did.

First, it is simple and to the point. There is no reason to over complicate things for these idiots. Too harsh? Sorry not sorry.

Second, I read back through the HOA Bylaws. The document clearly states if there is any time the HOA denies a request for long term rental, they must provide a detailed explanation of how to get the rental to be compliant. Here is the excerpt from the Bylaws:

In the event the lease is disapproved, the Board shall notify the Owner of the requisite action to be taken in order to bring the lease into compliance with the Declaration and any rules and regulations adopted pursuant thereto. If the Board does not provide an approval or disapproval within the time period set forth above, such lease shall be deemed approved.

This clearly states they need to provide more details than a simple denial. I wish I didn’t spend an hour reading through the Bylaw documents to find this, but sometimes you just want to educate yourself.

Kind of like this HOA/Board needs to educate themselves on what they have the authority to and not to do.

More Time Passing By And Gone Forever

I continue trying to keep my head up and not get frustrated. The longer they continue delaying this, the longer they are causing damages to myself.

It has now been 36 hours since my last follow up email to the board and HOA. Now time, for a follow-up on the follow-up. No reason to stop till I get a legitimate answer.

Here is the follow-up to the follow-up:

A response to the above would be greatly appreciated.

Also, if you can clearly state where in the Declaration and/or Bylaws it states the HOA/Board having the authority to not allow me to rent my place long term, it would be greatly appreciated.
Specifically, if you could call out the document section and excerpt that allows this action by the HOA & Board.
Thanks for your time, I look forward to hearing from you soon regarding this very important and time sensitive matter.
I know what you might be asking at this point. No, no, no. I don’t sign my emails with YRB ahah.
I put my actual name. Maybe Arthur, Ken, or Bob as @eoab__ calls me 🙂
Now time for more sit back and wait time. I wish this story would end, but the amount of email communication has been interesting. If they were to answer the actual questions I am asking, this would all be over. But since they have yet to answer my questions, I will continue pushing on this!
Now time to sit back and wait for their next response. Hopefully the next response isn’t another 48 hours away!

If you aren’t already, don’t forget to follow me on Instagram!

Thanks again for all the support and continuing to come back each day for new updates in this saga!

Want to checkout the latest on the saga with Ol’ Faithful, click the link below!

Ol’ Faithful HOA Saga – Final Path Forward With HOA Dispute


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How Much Clearer Do I Need To Make Myself – Asking The Same Question For The Third Time

I have had zero luck with this HOA to this point. How much clearer do I need to make myself. I have asked the same question for the third time now and they continue to not want to answer the specific question I am asking them. This is not only frustrating, but they are using this tactic to continue buying them time. I am a real estate investor, and have been a real estate investor for the past 3 years. This is the first time in my real estate investing journey that I have had issues with an HOA. I never would have imagined to have these issues with a HOA. But now that they are here, I am definitely taking this as a learning opportunity to continue getting better! What doesn’t kill you only makes you stronger if you want it to make you stronger!

Get caught up on everything that has happened to this point! This has been a wild journey to say the least and it is definitely not over! Below are the links to all the craziness in this saga!

Quick Recap Of Where We Stand

It has been a wild real estate investing journey up to this point. Now time to give a quick update on where we are at. The last email I sent to the HOA was clearly stating the pivot I was making on my business model. It is clear based off the Executive Order from the governor that no short term rentals are allowed anymore. At least while the Executive Order is in place.

I decided to pivot my business model into rentals of 30 days or more. To my knowledge, there are a few things that need to be true about your property for this to be legal:

  1. You can’t have it listed on short term rental sites
  2. You have to advertise it as 30+ day rentals
  3. For my situation with this HOA, any rentals between 3-6 months must be approved by the HOA/Board.

Awesome, now that we know where we stand, time to dive into the HOA/Board’s response from my latest email telling them I plan to pivot!

The HOA/Board Response To My Pivot Email

Now time for more fun, this time, a few back and forths with still a lot of frustration from my end.

In my last email response to the GM and Board, I clearly articulated why what they explained was misleading to all homeowners. They are simply creating more confusion than they are helping the situation. Especially for homeowners who are investors and don’t live in the area, which is the majority.

Here is the response they had to my last email:

Good Afternoon YRB,

We are working under the premise that EO-87  (Emergency Management – COVID-19 – Vacation Rental Closures) ends tomorrow. If the ban is not extended or a new ban issued then new guest rentals will be allowed entry as of Saturday.

Please note that clubhouse amenities will remain closed until further notice.

Thanks and stay safe.

Well, that response literally didn’t answer the only question I had. I clearly stated why their first email was misleading and then asked to rent my place long term. They don’t even want to think of offering other alternatives to investors, instead, they simply outlined the fact that they would allow new guests in once the ban is completed.

Here is the simple fact that both them and myself knew. There was a 99.9% chance the governor of Florida would sign an extension to the ban on the day of expiration of the first executive order.

Here Is What Is Frustrating

I usually can keep my cool pretty well. In this scenario though, the HOA/Board took over 48 hours to respond to a simple question. Not only did they take over 48 hours, they didn’t even answer the damn question I asked them to answer!

They knew the response they sent would just allow them to kick the can down the road even longer. Not to mention the fact that I am sure they are fed up with me at this point. I continue to point out holes in their arguments and they believe I won’t seek further damage because of the actions they have taken. More to come on that front.

In the meantime, I decided more email communication would be necessary to get a very clear direction to the Board/HOA on what I wanted them to answer.

My Follow Up Email

I was tired of them giving me the run around again and again and again while they know they are not doing the right thing. Time to be extremely clear on the ask…AGAIN!

Here is the email response I sent back to them:

Thanks HOA GM. 

I would like to ask the question again about long term residents as the law states long term rentals are still allowed. I will ask the question again for the third time and try to rephrase it in hopes this will help you understand what I am asking. 
This is in regards to long term residents, not short term. 
Regardless of the Executive Order being extended, are new long term tenants not allowed to check in and stay at my place? 
Thanks for your time, I look forward to hearing from you soon regarding this very important and time sensitive matter. 


If this isn’t clear enough, then I don’t know what is. I didn’t state anything but the fact that I want to know if I can rent long term.

Ok, now for their response which was again delayed for over 24 hours!


As per our Docs there are no restrictions on guest staying from 1 to 90 days.  Owners are allowed to make reservation for up 90 days. Guests staying from 90 days to 6 months will require HOA approval prior to check-in. And as per our Docs no guests are allowed to stay beyond 6 months.

Hope this answers your question.

I have been overly patient with the HOA and Board. They are continuing to dance around the question. There is only one reason they are continuing to stall. Because they know they are not abiding by the law and they have no grounds to stand on here.

My Hair Continues Falling Out By The Minute

At this point, I just hope I am right about the pivot I have determined to be legal for me to make. My understanding is 30+ day rentals are allowed in Florida and I continue to get the runaround from the HOA because I think they realize the bullshit they have gotten into.

I am still a firm believer they are doing this because they think I won’t seek damages for them to pay.

Time for another response back to the HOA:

Thanks for the response.

This doesn’t answer the question if I am allowed to rent my place long term under the direction per the latest email sent from the HOA. The direction makes it clear that no new guests are allowed into the resort. 
Long term rentals are still allowed per the law. If the law permits long term rentals, does the HOA still stand by not allowing any new guests and not abiding by this? If so, could you please point to what specifically in the HOA Bylaws and/or Declaration documents give the HOA the authority to create restrictions beyond the executive order?
Thanks for you time, I look forward to hearing from you soon regarding this important and very time sensitive matter.
Oh yeah. I went there. If the HOA is not allowing any new guests in, could you please send me where in the Bylaws/Declaration documents does it give them the authority to do so.
Now time to sit back and wait for their next response. Hopefully the next response isn’t another 48 hours away!

If you aren’t already, don’t forget to follow me on Instagram!

Thanks again for all the support and continuing to come back each day for new updates in this saga!

Checkout the next post in this saga below!

How Many Times Do I Have To Repeat The Same Thing – Real Estate Investing Problems

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The HOA Facebook Group Gets Heated – Time For The Popcorn!

I honestly thought the HOA facebook group wasn’t going to have much more fun stuff to post about, but boy was I wrong. The below is a full unedited version of the conversation that spun up the other day in the Facebook homeowners group. The hilarious part of this story is the fact that the individual who spun it up was one of the individuals who complained about me wanting to rent my place long term. And now she had the nerve to make this comment, and it lit a flare and a lot of fiery conversation!

Before hopping into this incredible exchange on Facebook, get caught up on everything that is going on! If you haven’t caught up yet, start from the beginning of the story to get the full craziness of this saga with my HOA!

Time For The Fun!

Facebook Pic Pic

The Message That Kicked Everything Off!


Now the fun shall begin!

FBTV Pic 2

First they begin complaining that the HOA turned off the lights at night at that was causing a large safety risk for the people who live onsite. Hmmm…interesting. Someone even mentioned they wondered what happened to the guests that arrived at the gate from my home. Since I haven’t posted anything in the FB group stating what happened, I am for sure certain people think I am still trying to force people in.

FBTV Pic 3

Now the accusations begin coming in with accusing homeowners for breaking guests in “illegally” to the resort. Again, it isn’t illegal. I am allowed to rent my place 30+ days. Period. And this stall that the HOA on is insane.


FBTV Pic 4

More accusations accusing homeowners in the resort who are investors whom are still renting out their homes.

FBTV Pic 5

Okay, this is where I have to step in. This lady who is the one who posted on the top of the above picture is full of s**** and the biggest hypocrite I think I have ever seen. So first she complains for people’s safety in the resort for having strangers come in and stay for extended periods of time.

The day after she said all that, someone reached out to me with a link to a Facebook group and told me to check it out. The link ended up taking me to a Garage Sale Facebook group in the Orlando area where this same lady had posted 5 things every day for the last two weeks to sell. Not only had she posted 5 things, but she was openly telling people where they could meet up to complete the sale of her crap. 

Yeah, I laughed out loud for a good hour after I heard and read all that crap.


More fun accusations!

FBTV Pic 6

FBTV Pic 8


And now the head of the board weighs in. I lolled at this one as well.

FBTV Pic 9

I won’t even give me 2 cents as to the nonsense I just read over again. The way they are going about handling this situation is, pathetic.

FBTV Pic 10


Ok, there was my one comment above. I just couldn’t hold back anymore. My one and only comment in thread though! It was extremely hard to keep my fingers from hitting send on a few different comments I had queued up.

FBTV Pic 11

So that is where this part of the story ends, but my fight and battle with the HOA is not over yet!

In tomorrow’s post, I will post a few different back and forths I have had with the HOA now. These back and forths have been extremely frustrating to say the least and how they have handled responding to email has been horrible. 48 hour response times is not acceptable. They continue to try to just drag this out till they have to let me rent my place out because then the “ban” will be lifted.

More to come…don’t worry. This is not where the story ends!

If you aren’t already, don’t forget to follow me on Instagram!

Thanks again for all the support and continuing to come back each day for new updates in this saga!

Checkout the next part of this saga at the link below!

How Much Clearer Do I Need To Make Myself – Asking The Same Question For The Third Time