We were thinking of selling our current property and maybe getting 40-50k from that and adding it to our saved funds as this property is probably not the best to have in the long run. 

In Virginia, the deed of trust usually contains the advertisement procedure; if no procedure is prescribed the advertisement must run for once a week for four (4) weeks.

I am getting ready to return to Jax to run my job sites if you need any advice feel free to P.M me.

I know of HELOC, delayed financing, and FHA (203)k loans but I'm not sure these will maximize my investing potential in the long run and I don't plan on living at the property.  

The entire process can run from $5k-$100k in severe situations (I've only witnessed one such repair cost that high).

This would all then possibly be run through an LLC to manage the short term rentals.

I had an O & E run and it shows a DOT and a mortgage of $56,000 borrowed 33 years ago.

This one is by no means a "home run" obviously, cause it'd be gone by now if so, but what i'm wondering is this: what if the right purchase price could make this an 8/10?

You may want to run some test ads.

However, you do run into issues of how you find the property to get under contract.