It conforms to recent changes in the law and also implements my approach to managing property. 2.

He has 20 units all right together on the side of a mountain, meaning it's probably easier to manage.

You can purchase rental properties from them and they manager the properties as well. 

But they all are managable.

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. 

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.

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

Assemble a team of individuals who can split following responsibilities: contribute the earnest deposit money, guarantee the loan, find the deal/conduct the diligence, raise the capital and manage the building.

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