I've read the Long-Distance Real Estate Investing book, but still uncertain that I want to start there.

I currently work for a luxury building materials company and my commute is about an hour and a half each way every day.

Start remote with some commuting back to Chicago? 

Offer to pay the neighbors a reasonable amount say $50 - $100/mo. as they're doing you a GRAND favor helping you and besides that extra money may aide with commuting costs to work or a boost to their monthly budget or a their savings account!

All that being said I love living in the area it is close to Destin and the bases and very close to the water, much of the city is walking distance to a the water. 

North Suffolk I'm more likely to flip; downtown I'll most likely rent; south can go either way but due to driving distance and no property management I'll probably flip.

Option B: I might consider this if I know the listing agent and property is within driving distance.

There is an Air-force base and other aerospace companies which I believe is much of the clientele there but from my experience most people will live in the Antelope Valley or Rosamond and commute to work out there.

We work in NYC and need to keep the commute under 90 mins, but will consider any good investment in that radius (think New Paltz as the northern limit).

Sherrils Ford vs Mooresville - I like the location of Mooresville wrt commuting, etc.