My concern would be late night visits to an area I might fear for my safety in.  

But once you start talking about a "complex", then fear and doubt set in.  

Unless the fear of losing the job or losing future jobs is motivation enough.

I've always wanted to do more but fear and lack of resources kept me on the side lines.

Make sure you haven't negated your hazard or title insurance by quitclaiming  your interest out of the insured asset.Much more likely to need the insurance than protection from the 1 in 18 million slip and fall suit everyone seems to fear.

My biggest fear is once I find my first deal I won't be able to find a contractor.

So im not to scared with the area i take not that i will always have fear due to my generalised anxiaty disorder.

If this was a major fear of yours you would have to get a seperate LLC for each property (which would be quite expensive).

I hesitated for a few days before calling for fear of getting rejected by this man because he has known me since I was a kid and I used to work for him while in Middle school.

Let your "fear" become your driving force!