Greater Sarasota County allows 30+ rentals, but nothing shorter.Lakewood Ranch was "up and coming" in 2004 and is a great master planned community but probably is not ideal for STR as there is no natural draw. 

My advice on investing back in the states is definitely make sure you have someone back there you fully trust (preferably with a stake in the properties success) before you do.The Tokyo Brewdog monthly meetup can be a good place to get some details on what's out there but be wary of everything you are told as Ivery found a lot of info I was getting wasn't entirely complete and found myself discussing more in some other circles with friends and colleagues these days.Happy to talk specifics sometime of you have questions. 

If you plan to sell within a few year of making it your primary then don’t do the exchange until a couple years before you move in.

It's up to the City and their zoning/planning requirements.

And since i have a very specific niche and pricing structure I am always the last one they call and the clients usually have run out of time and are going to lose the deal and their deposit if they cant close in 3 to 5 days.. :)  So i turn them to yes or no in 24 to 48 hours so i dont hold anyone up.Just had one today  Pacific Palisades land deal  appraised 50mil but guy will take 20 mil if we can close in 10 working days.. needs dough for a deal in Vegas..

If everyone is on board with the plan to wholesale the deal, you are responsible for finding an end buyer and assigning the contract.

App_mode=Displ...Also, our Governor Ron DeSantis just passed a "Squatter law" which always a homeowner to reclaim their property INSTANTLY under these terms The individual has unlawfully entered and remains on the property;The individual has been directed to leave the property by the owner but has not done so; andThe individual is not a current or former tenant in a legal dispute.First in the Nation to do so.Link to squatter article - https://www.flgov.com/2024/03/27/governor-desantis-signs-leg...Let me know if you have any questions about FL or plan on investing in the Sunshine State!

Afterwards, the plan is to utilize my VA home loan to buy a multi-family property.

As far as being able to use your Roth you should be able to, or at least buy into a fund, but contact your plan administrator to find out for sure. 

Depending on how you are planning to pay your friend  the profit out of the transaction.