That being said- in sarasota FL, I would say no way.

As another licensed contractor, I’d love to tell you how many messes I clean up in houses from fly by night hammer swingers.

I'm looking at data like job growth and migration.I'm going to continue this routine until the end of the year before I even consider doing a deal out of state (partially out of necessity as I have a few huge development deals out here that I'm finishing up).Once I hone in on a few pockets that look promising, I'll be flying out there to drive the area and get to know the region in real life.

But I will consider flying out to see it. 

Do you want to fly a plane?

Do your homework up front and see which ones have been around a long time and not "fly by night"  Check reviews (although many times disgruntled tenants will post bad reviews)The reason you pay a property management company is to maximize profit, oversee tenant placement (including intensive screening), rents, maintenance, late letters, leases - how to give notices according to the landlord tenant code where your property (or properties) are located. 

I do not have time to work on a property (or even fly out for closing, etc).

It's like handing someone a plane, a tank of fuel, and a "Piloting for Dummies" book and wondering why they can't figure out how to fly a plane on their own. 

I am flying out end of May/beginning of June.

I think part of this is people are wanting to do driving isolated vacations rather than flying to busy destinations.