All Forum Posts by: Joshuam R.
Joshuam R. has started 40 posts and replied 257 times.
Post: Is Florida a good market to start a STR

- Specialist
- Florida
- Posts 270
- Votes 91
Quote from @Ashek Elahi:
Hey everyone, I am looking for information about Florida market, seeing how the houses are so pricy (Dania beach, Hollywood, Miami area)
what would be the best strategy to start a STR with out having to fork out all my savings in one property. I been making calls to houses thats been on the market for 60days or more but nothing is working. is there anyone that is currently doing STR in the FL market that can give some tip where would be a good place to start and what I should expect.
Thank you in advance.
Cheers!
Hello Ashek,
If you're starting in Florida with zero properties, your first DBPR (Department of Business and Professional Regulation) vacation rental license will almost always be a single-property license. This license can be issued either in your personal name or under your LLC. If you want to run your short-term rental operation like a business from the very beginning, it's better to have the lease and license under your LLC. That way, when you scale, you won't have to go back and redo all your licensing paperwork.
Florida's DBPR offers three main types of licenses: Single, Group, and Collective. The single license covers just one address — you'll need one for each property if they don't qualify for grouping. A group license applies to multiple units within the same building or connected buildings under the same ownership. The collective license is what most professional operators aim for, as it allows multiple properties in the same county under one license, provided they share the same ownership entity (like your LLC). This can save time and money, especially when managing several units.
While it’s true that many short-term rentals in Florida operate without DBPR licenses, that doesn’t mean it’s a smart move. Operating unlicensed is technically illegal. Fines can be as high as $1,000 per day, and enforcement actions can include cease-and-desist orders or even removal from platforms like Airbnb. Some areas in Florida are strict about enforcement, especially major tourist destinations such as Miami-Dade, Orange, and Pinellas counties. Others may be slower to enforce, but that’s changing as local governments strengthen their short-term rental policies.
A common reason unlicensed rentals fly under the radar is because platforms like Airbnb don’t always verify DBPR license numbers unless there’s active enforcement in that jurisdiction. However, enforcement usually ramps up quickly once there are complaints from neighbors, reports from competing hosts, or safety incidents at a property. If you’re doing rental arbitrage — meaning you don’t own the property and rely on a lease agreement — you’re even more vulnerable. If your landlord receives a violation notice, they might simply terminate your lease to avoid trouble.
For anyone looking to operate professionally in Florida, getting licensed from day one isn’t just about legal compliance — it’s also about credibility. Landlords are far more likely to approve your short-term rental proposal if you present yourself as a licensed, compliant operator. Plus, starting correctly means when you grow from one property to several, you can easily transition to a collective license without having to redo your legal and administrative setup.
Post: New Member looking for opprtunities / strategies to start out STR - Rental Arbitrage

- Specialist
- Florida
- Posts 270
- Votes 91
Quote from @Shawn McCormick:
Sorry about your situation. I totally agree with @Michael Baum, you really don't have options unless you could do a HELOC, depending on if you have any equity or if you 'overpaid' for the house last year. Unfortunately, Deltona isn't close enough to Disney to really do well with Airbnb. I do have friends that are successful in Sanford, Deland etc, but it is harder.
If you are really in a bind, maybe consider selling your house subject to the current mortgage (this will only be attractive to a buyer if your interest rate is 4% or below since the mortgage is still so new AND you have equity. IF...that is the case, you might get enough cash to go buy a multi family and have a better shot.
As far as DSCR, they are higher interest rate and generally 20-25% down payment (some exceptions could get you in with 15%), so that is definitely not an option for you. If you are a Veteran, you could use your entitlements for a VA loan (0% down) Parts of Deland are eligible for a 0% down USDA loan, but the requirements for you are higher (credit score/income limits).
Hope this helps, best of luck.
Your friends dealing in Sanford and Deland, is it owned properties as STR or running it via arbitrage ?
Post: New Member looking for opprtunities / strategies to start out STR - Rental Arbitrage

- Specialist
- Florida
- Posts 270
- Votes 91
Quote from @David Jean-Georges:
Quote from @Shawn McCormick:
Sorry about your situation. I totally agree with @Michael Baum, you really don't have options unless you could do a HELOC, depending on if you have any equity or if you 'overpaid' for the house last year. Unfortunately, Deltona isn't close enough to Disney to really do well with Airbnb. I do have friends that are successful in Sanford, Deland etc, but it is harder.
If you are really in a bind, maybe consider selling your house subject to the current mortgage (this will only be attractive to a buyer if your interest rate is 4% or below since the mortgage is still so new AND you have equity. IF...that is the case, you might get enough cash to go buy a multi family and have a better shot.
As far as DSCR, they are higher interest rate and generally 20-25% down payment (some exceptions could get you in with 15%), so that is definitely not an option for you. If you are a Veteran, you could use your entitlements for a VA loan (0% down) Parts of Deland are eligible for a 0% down USDA loan, but the requirements for you are higher (credit score/income limits).
Hope this helps, best of luck.
Deltona is just a very awkward layout of a town, even to live there. Deland has that small town magic, springs, nature, fishing, direct route to Daytona beach, new Smyrna, etc.. Sanford is key due to the lively downtown and the Airport. Hope you kept firm in seeking your opportunities and knowledge since your last post. Best wishes.
Post: Short Term Rental arbitrage in Orlando, Florida

- Specialist
- Florida
- Posts 270
- Votes 91
Quote from @Daylon Pritchett:
This is fantastic advice Tony. Thanks so much for your response. I have continued to move forward with my pursuit of STRs.
Thank you!
Daylon
Tony is correct. Unfortunately anyone doing it actively in Central Florida has not shared their success story.
I can see with research it is impossible to do it legit. But I bet a few are doing it as a grey area and for a few years. These are the ones we want to hear from as I do my self.
Post: Short Term Rental arbitrage in Orlando, Florida

- Specialist
- Florida
- Posts 270
- Votes 91
Quote from @Daylon Pritchett:
Anyone successfully executing this strategy in the Orlando market/surrounding areas? My partner and I have found one landlord that will allow us to sublet to our business travelers and Leisure travelers. But many have not. Any success stories/best practices?
How is this going for you today in 2025 since then.
Post: April 9th 2024 Case study - Yes or No

- Specialist
- Florida
- Posts 270
- Votes 91
15yr Fixed equity loan base rate could be as low as 10.25% at 100% loan to value, with a base APR as low as 10.25%. With a promotion of
Navy Federal will pay for closing cost and appraisal if needed. So all you might end up paying would be small fees not part of closing, title, settlement, etc.
example $68,457 would be $745.15 a month.
Who are actively pursuing such equity loan products? and or your thoughts on this.
Post: Advice on my STR pitch and overall Rental Arbitrage advice (Alexandria VA)

- Specialist
- Florida
- Posts 270
- Votes 91
Quote from @Fakaradin Floyd:
Quote from @John Underwood:
Quote from @Cody L.:
Quote from @John Underwood:
How long is your lease with the owner?
What happens at the end of the lease if the owner realizes that they can just take the property back and do what you are doing?
I have tons of my units leased by people who do airbnb. We don't take them back. Why? We don't want to do what they do. We want our rent check every month. Airbnb is not our business. My guess is it's not the business of this little old lady he's renting from. She's not trying to be an airbnb operator. She just wants a monthly rent check.
I agree. There are no guarantees other than this 12 month lease. People even break leases all the time.
The lady could decide to manage her self, she could get hit by a bus and her Heirs realize the STR person is making too much money off their property. Some one could offer her a better deal with profit sharing. These are just a few things that could happen.
The Arbitrage person is not the owner of the property therefore has limited control over possible outcomes that may or may not happen.
These are just the facts.
@John Underwood
I hear you John, I am not disagreeing with you honestly I just wanted to showcase my accomplishments thus far, I am not thinking in the case of what can happen and thinking of the cases of what I can keep in control of.
You bringing up an owner can break the lease, someone could die and the family takes over, she can get a better deal profit sharing. These are what-ifs and usually lead to anxiety for a lot of people. These risks can happen to anybody no matter the type of investment they make like your investment house can blow up and insurance doesn't accept your claim, you could get hit by a bus, and boom no money, and so on.
It's not really a fact of the world but a risk a real risk correct but its a what if, and if I laid in bed after successfully setting up an Airbnb arbitrage and so far have success and just think about what if this or what if that, it'll only slow me down.
Those what-ifs only matter when they happen, anxious thoughts really aren't something I put an extreme amount of thought towards since the majority of the time they slow me down and result in an analysis paralysis type of scenario. You can only do so much to prevent worst-case scenarios
EXACTLY!!!, Deal with the what-ifs, only when they happen. Before they happen prep a little cushion here and there for different areas you have your hands on.
Post: Syndication Attorney costs

- Specialist
- Florida
- Posts 270
- Votes 91
Quote from @Amy Wan:
Hi, syndication attorney here. First, it depends on what you're doing. Most folks do a Regulation D offering (rule 506b or 506c). For that, its 7500 to 25K and up. If you're doing something else, it depends. A Reg CF (which I dont recommend folks in real estate use) can be a couple thousand. A Reg A+ offering can start at 35-50K, though I once saw an attorney charge 500K for it. So, it depends.
Thank you @Amy Wan, what would be your fee or average fee cost to establish a syndication only to be offered to non accredited friends and family. No advertising. Regulation #??
Post: Controversial Take: Reading Books = Overrated

- Specialist
- Florida
- Posts 270
- Votes 91
Has to be a combo hit , you read one book or 100 books or 1,000 books it will only count as 20%
The other 80% has to be hands on action = success + growth.
Post: Hold primary mortgage, But add a friend on title.

- Specialist
- Florida
- Posts 270
- Votes 91
In regards to the mortgage you are correct John, It cannot be a loan. A letter must be written to show it as a gift.
In regards to who you put on title it is separate. But yes, I did missed the equal shares, vs specific shares via LLC.
It is NFCU, zero down-payment product, they do not care about seasoned funds in accounts. But underwriters would ask about big deposits , to make sure is non-criminal activities they required a letter stating is a gift and not a loan from such party.
Regardless of the loan product, and using your explanation as an example would this be the outlook: Title to include Person 1 (mortgage holder) + LLC (93% Person 1 + 7% Person 2)