Based on my research it seems like with a little rehab and managing a short term rental effectively, short term would likely cash flow more in a market like Tampa. 

Since you appear to live in Brooklyn I assume you will rely on a 3rd party property manager.

I wanted to self manage, and hence was thinking of focusing on the areas close to where we live.

House hacking will also give you some personal "property management" experience.

Learning to manage tenants, property managers, and projects is a whole other set of skills.

Biggest suggestion would be to make sure you are flexible, willing to work with multiple housing programs, and hire a good manager if you are not going to self manage the units.

It's a good idea to talk to legal and financial experts about taxes, insurance, liability, rental agreements, and managing your finances.

He replied, "I don't know how you keep finding sellers willing to do that".Here is the secret sauce, know and understand the seller's motivation, ask questions, and don't be afraid to ask for the terms you want.It is more common in medium-sized multifamily where it is a business but not large enough to be professionally managed.

I was originally going to manage the project myself and sub out all of the work.

For these elusive big fish, I'd drive out to the property and talk to whoever's managing it.