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 Ohio market is very strong and competitive, so people struggle to find deals with consistently great margins on flips, etc.

Just know that it is a "no days off" kind of business and very mechanical.I would suggest documenting your process via video so that eventually you can bring people on to replace the different hats you will be wearing.Keep in mind of these 5 components of any wholesale business.lead generation, deal sourcing, underwriting, marketing, transaction coordination.

Now let's say one or both people making the purchase owned a condo previously where they roll over the proceeds/equity into the new purchase and put 40% down.

I think other people seeing makes me feel accountable to post along with having it written out.

How would you like to be a tenant waiting on a repair because the owner wants 3 bids for everything and not only will that delay the repairs, but you'll have 3 people coming through your home everytime you make a maintenance request?

Some questions for the people with experience: What are some basic landlord problems I will most likely run into?

With the cost of utilities and the level of comfort people feel is mandatory now there is no way I would want to be on the hook for it. 

Yes, you need a team, however you can't just assemble people together and call it a team. 

Jorge is putting out a letter in a week or two with specific numbers people are asking about.