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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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3 Reasons You Need Many Income Streams

This topic hits hard since something recent at work. You need many income streams in your life. Period. Having many income streams is critical to your long term financial success. I recently had to displace an associate who was working for me. This was an extremely difficult thing to do. This decision wasn’t made by me, but rather the larger business. This got me to thinking, if I were to get displaced from work tomorrow, would I be okay?
What I Mean By Many Income Streams
Here is the simple way to think about it. Your 9-5 job is an income stream. Anything else that produces monthly cash into your pocket is an income stream. You can checkout this article I wrote in the past about different horizontal income streams I currently have
If You Were Fired From Your Job Tomorrow, How Would You Make Ends Meet?
Have you ever thought about this? Most people don’t, but the recent experience I had started the wheels turning. The majority of people are reliant on one source of income. This source of income is typically their 9-5 day job. There is nothing wrong with this approach if you are employed and want to be employed the rest of your life. In this sense, you are exchanging your time for money.
Again, nothing wrong with this approach as long as you realize what you are signing up for. People with one income stream are dependent on staying employed. If you were to get displaced, you are putting yourself in a dangerous spot.
Nothing Is More Powerful Than Having Control Of Your Destiny
When you are dependent on one source of income, once that stops, your income stops. Let that sink in. When you are dependent on one source of income, once that stops, your income stops.
If there is one thing I have learned in the last year and a half, it is the importance of having many income streams. Over the past year and a half, I have been working hard to develop many income streams. The end goal for is to develop income streams from investments that become greater than my W2 income in the next 5 years.
Key Takeaways:
  • Evaluate how many income streams you currently have. If it is one, that is fine. The goal is to understand if you are reliant on a single source.
  • Having control of your financial destiny with many income streams allows you freedom.
Don’t forget @TheYoungRetireeBy33 3 Core Principles: