Is this the norm or either I sound too friendly and he's trying to be nice and help me out(that's a stretch) or the more likely one - do I sound so inexperienced (which I am, inexperienced that is) and he just wants to make sure he'll get paid?

If the house has equity, why not try to take out a HELOC and perform some of the repairs while the renter is still there?

http://www.marcusmillichap.com/Email/news/2016_05-...Emerging supply and demand trends for residential and commercial real estateHow brick and mortar retail is performing in light of rapid rise in e-commerceWhat investor sentiment says about the future of real estate markets

Performing or non performing?

I don't anticipate a contractor to perform his craft any less effective just because we needed to cut costs.

Receipts for work performed by other professionals should be provided before work is paid.  

Based on the information provided, you were fined for performing plumbing without a license, not that something was wrong with the plumbing.

Has there been extensive physical improvements such as a total rehabilitation of the structure?

A contractor, in the eyes of the law and anyone with contracting experience, is simply someone who enters into a contract to perform a service or supply goods.

Even though you aren't the one occupying the house, it is your credit and character 'guaranteeing' performance.