As @Mike Verna mentioned above, demand for certain properties is key.

I am also relatively new to the area, so I don't have a great feel for the local market.From what I can see, it appears to be highly competitive at the moment, and there aren't any turn key properties at my price point.For all the experience investors out there,If you found yourself in this situation, which strategy would you pursue?

Mat Zalk @ key renter is the best in the biz! 

A mobile phone app is key so you have persistent access no matter where you are.Total operating cost (coverage, cost of exports, cost to acquire additional contact or transaction history data) factoring in assumptions in overall marketing effort and volume.

I gave property management over 2 months notice before I moved out and they said that they would try to re-rent my unit, but until then, I would still be responsible for my rent per my original lease agreement.After a month without any contact or updates, I just got an email from property management asking that I return my keys despite the fact that my lease is still active until 8/31/18 and I'll be paying rent until 8/31/18.

Just bail....cash for keys.....I wouldn't be surprised if 75%+ of bad tenant "endings" don't go down as a legal recorded evictionHe lied....knew he had an eviction....he didn't forget it.....he lied about a subject that is very critical in the screening process.If he had told you 'hey I had an eviction 14 years ago, but here are my last 3 landlords contacts so you can call for references" then I may let it slide once I check his storySo unless this guy is a superstar in every other screening category, ....AND my tenant pool is otherwise junk.....I would 100% pass.....

@Daniel WinsorI am not local to Key West however I spend a month or so there each year.

I live in Northern Virginia and I am looking to invest in turn key properties in a few markets in other states. 

It sure sounds like the inspection will be key here.

I guess what I am trying to ask is:1) Would you go for 5 houses or 2 duplexes  or whatever that bring you 1.5K cashflow in the middle of nowhere  (key word middle of nowhere)2) would you buy one fourplex 1 hour away from a big city that cash flows 1kI guess what I was trying to compare is would smart people go for:  1) close (1 hr away) to  big city property  (cashflows 1K)or 2) a little bit more cashflow from middle of nowhere?