The one part of your post that I might do is "the places to stay" part. We did have family and friends put us up. We also had friends or family arrange for someone they knew or were related to put us up. Asking for money is a no no to my way of thinking unless it is going to a charity and even then I find it questionable.
Check out warmshowers.org and couchsurfing.org for hosts. Also we managed to camp for free much of the time in that part of the country, definitely better than half of the time. In towns big enough to have police I asked them first, but in small towns I often camped in the picnic areas of the town park. If that seemed iffy for some reason I asked around and sometimes wound up being offered a different place to camp like at a church or in someone's yard. When in doubt I tried to set up my tent in plain sight early enough that I would know early on if I was going to be kicked out (never have been though).
Other places to ask if they know where you can pitch a tent for the night are firehouses, the general store or minimart, the public library, the wait staff in the diner or just about anyone you meet. This seems to work best in very small and relatively remote rural towns, but I have had some luck camping in a larger city park as well where we asked the park manager in a large-ish city park and he let the police know we were OK to be there and arranged it so we could use the pool and showers.
If we pay to stay, we usually explain that were are on a tour from ____ to ____ (I think the longer the tour the better your chances) and ask if they have a cyclists discount. Often that resulted in some kind of price break. Barring that, if you qualify for a AAA or AARP discount most places offer some kind of price break.