Because of #2, if it's true that you're only allowed to do 1 deal per year in Chicago as an unlicensed person, I would not pursue wholesaling.

Of course not and those can be some of the best deals ever.Let the unlicensed lender screw up on the paperwork... might even create a defense or right to rescind, setoff, etc.

I read an interesting article on PA laws as it pertains to licensed and unlicensed real estate transactions and deals.

I go back to if someone is to use your unit as an STR, why choose an unlicensed, uninsured, low asset  arbitrager over a licensed, insured, professional PM that has a team of employees, lots of experience, a grand network, etc.?  

Curious to hear what insurance professionals and attorneys would say about this, my suspicion is that unlicensed wholesalers inevitably take on a certain amount of legal exposure (and licensed wholesalers also for that matter, nothing against it personally but it's part of the deal when wholesaling IMO). 

In addition to that...banks are going to have a hard time doing any sort of financing to an unlicensed person.

The penalties for renting an unlicensed English basement can be severe, and every tenant in DC is eligible for free legal help if they find out they're in an unlicensed rental. 

Thoughts? Anyone have experience with this in Florida?

Details:
-Property currently under contract with a wholesaler at 76% of ARV.
-Rehab included new driveway, addition of bathroom and converting a room to bedr...

When your a merely a intermediary, unlicensed, operating in a gray area, you lose your leverage. 

You can probably find an unlicensed guy to do it for about half or DIY for about a grand, but both of those come with their own risks.The only requirement is that it must have permanent heat.