His brother (the squatter) wasn’t going to leave the property without a fight.I showed up to the house with my acquisition guy, and things quickly got hostile.

This would obviously reduce my cash flow on both properties, as I would be paying the minimum HELOC payment plus extra towards the principal to pay it off quickly.

You may have to evict which is generally the course it goes but do something/everything (legally available) to cure this quickly. 

And a general contractor would NEVER sign a customers contract 

Being a landlord is not an overnight get rich quick scheme.

Hi Kin,Three quick questions come to mind that would impact your situation.

I manage hundreds of rentals and most of them are caulked every 5 - 10 years.DR Horton was the builder, and after we did two inspections and closed on the house, we found out that a good chunk of the roof was missing - they quickly finished the roofing. 

A prudent investor doesn't seek quick riches through shortcuts.

The house is worth at “quick sale” about $360,000.  

Plus doing a quick read did you include all Personal property in the calculation such as furnishings?