The house looked like every other house on the block and I wanted to fix it up without spending a lot, so I shopped Offer Up and Craigslist.

Mmm, that could result in couple of things, she might be a pain moving forward or she would be your perfect/dream tenant who is going taking care of the property and pays on time.

My issue is I'm not sure how often I should chase them without being a pain in the *** just to make sure my property is getting the attention I want it to. 

I'll use this as building blocks on perfecting how I interview and set expectations in other markets as I continue to scale.

On this case, the bid sheet information is blocked/removed, but you  can pm me for how to get around this.  

Your fear of not having a tenant is blocking the overall picture.

I too tried to use Hangouts and even Skype but, all people don't use it so... becomes a pain.

Being green in any new venture is going to have it's learning pains, and it's good to be honest with yourself upfront (which you seem to be).

There really is a town named Hell.At the end of the day trip, the driver was driving down a beautiful road in the jungle but we could see there was a road block at the end of the street.

Those are the two big road-blocks you will hit trying to use anything in the standard battery of mortgage products.