. $25,000 means the most expensive property you can buy is $100,000Without knowing your situation or location, consider house hacking.

I dont believe there is a way to locate vacant properties in the Orange County courthouse database.

If you are able to find a property manager who simply looking for their monthly rent, and you have done your homework for potential income for AirBnBs in that location (as well as being familiar with the ordinances in your area), you can negotiate a clause to be able to list on STR platforms. 

4 family gut rehab located in Tarrytown, NY.

The more experience the better.2) Location matters a lot.

I'm located in the greater Cincinnati, Ohio area.What do I need to make sure of in regards to the lease as I transition into self managing/owning the property?

Employers do take advantage of that to lease smaller office space in better locations. 

I am open to south Florida locations but for flips I prefer to stay in PSL, Martin and Palm Beach County.

Plus my initial thoughts for purchasing were strictly for a rental eventually, and I'm in a great A location next to so many things, and Portland has already started spreading out where I am and developing the area for huge growth. 

Like a broken record, the trick is to find out the perfect Location, Location, Location ;-) Many STRs break even or even lose money because the math needs to make sense in terms of year-round high average occupancy rates necessary to pass the break-even threshold.