The area has certain advantages like shelter from regulation risk (pretty much as low as anywhere in the country if you buy in the approved STR tourist zones) and long term security (people aren't going to stop going to Orlando anytime soon). 

The inexperience doesn't stop there.

If they are up for renewal and you elect to non renew them you must stop accepting funds from the occupants after the lease expires (accepting rent after the lease expires may make it appear you have a tenancy at will agreement). 

Quote from @Henry Clark: @Michael PlaksIf they want to stop money laundering and funding terrorism they can control the border.  

Stop hanging out with your deadbeat buddies who spend all day drinking, talking sports, and otherwise wasting away.

Some lenders allow exceptions for transfers to LLCs owned by the borrower, but it’s worth confirming first.Explore transfer tax exemptions: Chicago doesn’t make this easy, but there may be exemptions or reductions for certain types of ownership transfers.

Price RangeDefine your financial boundaries based on available capital and borrowing ability:For Class A & B, financing typically covers 75%-80% of the purchase price, allowing you to buy properties in the $6M-$12M range if you have $2.3M total cash.For Class C & D, due to higher risk, the price range might be reduced to $5M-$10M with the same cash.5.

For me as well as the seller.First, you have to define Sub to financing.Do you mean the reckless kind where you overpay for a property, take over the financing and borrow from others to cover closing costs and holding costs when you have no money, no credit, no income, no reserves and can't tell a warranty deed from a deed of trust and you close on the kitchen counteror do you meanbuying below market value, already having a nice income, having reserves, using escrow and title, already understanding the due on sale clause, have done a lot of creative purchases and know when to use and when not to use creative finance and how to recover if something goes amiss?

While this won't stop the Gen Y and Z crowd, I think it will make it harder for people to raise money, when a company with 30 yr track records are marketing right along side the guy with 2 yrs (for a similar type of deal).

I am wanting to be able to stop working full time sooner than later as I would like to be able to spend more time with my family and enjoy life.