Get to know the specific neighborhood, RE is hyper-local, there is no single market in any metro area, it is comprised of many micro-markets.

Quote from @Rowan Miele: When it comes to loans, check out FHA or conventional options, and maybe chat with a local lender for specifics. 

Hi, I am very interested in investing and  I would like to invest into short term vacation rental in Florida, preferably Kissimmee or Davenport. specifically in the community resorts.I live in NYC and i was wondering if investing  out of state is feasible?

Most cities have specifics like this for STR properties.

If you have specific questions feel free to let me know.

@Aaron Landauhappy to help, but you said you don't want the 'standard advice'... so what specifically are you looking for?

Having separate checking accounts (and credit cards) specifically for the rental properties might help the most as far as expense organization (and tax) accountability.

You can seek out a Realtor that is experienced in foreclosures if you already have a specific property in mind as you’ll likely need to move on it quickly if it’s already listed.I would advice to find someone local to help guide you.

Many flippers I know specifically don't have their license because of the following:  no need to follow Code of Ethics, sales isn't their skill, they are making money by sourcing deals not spending time doing sales (even of their own properties since it takes time away).Happy to chat if you like. 

Note that there may be nuances depending on the specific seasoning period.