Obviously we want something we could "force" appreciation into with updates, as opposed to betting on the market.

You can always offer more, or maybe, if you have your license, you can even work on a tiered percentage as opposed to a flat fee.  

That being the case they will usually rate you a little higher for those type of policies as opposed to your primary home / auto insurance that is getting a more preferred rate.

It could have been much much more if the circumstances were different but we had were replacing exterior wood with stucco and redoing the bath when we found this mess.

Do you look at exterior or interior first?

Please permit me to offer an opposing view, however...

Once the gutters get put on, the house gets painted, the new house numbers go up, and the new mailbox and exterior light go on, the house will look completely different!

It's in human nature to not care as much for something that they pay little on as opposed to an expensive rental space.

My question is since the mortgage company already includes the HELOC against me as they assume it will be drawn upon, would it make sense to pay off the high interest student loan and pay the now approximately $40 month on the line as opposed to $112 and would this lower my debt-to-income in regards to qualifying for a loan as my month debt obligations have now decreased?

Install Red/Blue strobe lights on the exterior of the building.