So much liability in this job nowadays has me looking for an alternate after my 20 years is up.

You can find everything on YT nowadays, or take classes at Home Depot. 

FB definitely works better than craigslist nowadays but actually meeting buyers is your best bet.

Even just hitting the 1% rule is really, really tough to do nowadays out here. 

Etc, Etc.....Pay after complete AND passed inspection.Some phases may require a payment in advance, like framing, electrical or plumbing.......a typical house will have a lumber materials cost of $15k (more nowadays :-) and it is fair for a contractor to ask for 50% so he can buy his lumber, and not be out that much.

When you say flat roof, hopefully you have a slight slope, because there are "flat" roof systems using modified bitumen (peel and stick nowadays) or tpo.

Lots of vacation rentals, casinos, and a military base nearby.Listed: 140K, Offered 140K (in my name as of now). 

What website or method do people use to find quality roommates nowadays?

Easy to find new renters nowadays....

Nowadays with technology, while you're sitting there, in the last 5 minutes you might have 3 text messages from agents wanting to hear back from an offer they sent 10 minutes ago.