For some reason I have a fear to take on any sept at all.  

I know a lot of fear and anxiety will go away after that first deal is made and buying the second will be twice as easy.

Anthony is correct that if you expect no appreciation, fear depreciation, and might want to move in short time....that favors the "rent" (and buy/sell transaction costs can really persuade you this way.)

Also, do not fear the eviction.

I'm currently trying to analyze deals in the area. but one thing I fear is overpaying for a property and thinking it was a "deal."

If they're a great team they shouldn't fear being totally transparent about hiccups and how they made it right. 

Given the state of the market, I am fearful of making mistakes.

Grab an investor who has shaken the fear off....AND GET TO IT!!

Feels risky, but am I just used to mediocrity and fear? 

The irony with this"fear of disturbing the neighborhood" nonsense is that hundreds of folks are already doing STR locally and no one realizes it!