Jamie, always enjoy your threads!
I try to keep things as legit as possible,as I don't need a real stupid trespassing charge or something on my record. So I don't stealth camp unless its a real emergency, ive only had to once or twice.
National forests are good, most allow camping anywhere you like as long as it is 300 feet from the road.
I feel comfortable setting up my hammock almost anywhere in a fairly secluded area, it's easier to get away with the "oh I just stopped to grab a nap" line in a hammock rather than a tent. Even a park, rest area, etc. Remember people in rest areas can take a nap in their car and you can't, so I've never had anyone give me a hard time about a hammock especially if one end of it is tied to the bike.
If its raining or the weather sucks and I can't find an actual legit place to set up my tent then a hotel looks pretty good at that point.