Lots of listings state seller will not do any repairs, however, if you uncover hidden items not present during standard initial walk through, you can certainly re-trade the price to cover the added costs.

At least have the decency to actually look at the property and of course we all use the inspection contingency to uncover unknown issues in attics, crawl spaces, basements and many other areas that require a full inspection.

I'd talk about how to structure deals to use a blend of seller finance, HM and or PM.

There are some options in Cat City that will be a good blend of lower price point, and substantial cashflow. 

If he uncovers any problem areas or something that he does not feel comfortable tackling I am going to go ahead and hire someone with a narrower focus.Again, thank you for the thoughtful answers, they played a role in this decision! 

What is the blended interest rate of the student loans? 

Your contractor should be the right blend of skill and pricing, often the cheapest one is not the best deal.

I'd look at the blended rate of your 1st now with what you'd be looking at on the HELOC, and compare that to the cash-out refi rate on a 20Yr Fixed. 

If your newer at this I would say why don't you consider blending the two?

However, I wish I went just to see first-hand what happens in these situations.I say keep following up to see what you can uncover.