If it add values, the property manager may hire you and pass on the cost...But I think where this second case is most likely is on larger projects (like 6-7 figures) and if you have some special credentials or skills like in construction project management, contractor and contract background, licenses, even engineer/architect, etc...

I had the same choice and I chose an attorney and it's only me.  

Good choice!

Consider a larger area, is the small town a bedroom community of a larger city, or is it miles away having to survive on its own population?

It was a business expense and an investment we were willing to make for good long term tenants.Since the unit you rent to them is currently uninhabitable, you could offer them some choices: 1.

Are you looking to grow your 50k into a larger portfolio? 

The good thing is: this is one problem that WILL solve itself with time ;)As to whether they'll trust you: there are a lot of intangibles about the choices people make.

I could go lower in property prices that I search for but those are in areas that most people wouldn't want to live in if they had a choice.

What I am trying to do is rent out the home I currently live in with the idea of buying a larger home with a bit more property.  

If you are going to invest outside your local area, you really should pick one or two choices and make trips and hook up with some locals in the area.