when i did my cross country moped trip, i found that a lot of the time being some place at the right time and instance provided me with more money and resources than i had planned. the short of it was that i wanted to take a trip with very little money to my name and see what happened.
now, i never ASKED for anything, but was often was given more than i needed. it started (and continued most of the trip) when i would stop for gas and to get feeling back in my balls. being on a moped with south carolina tags, i parked tags out most of the time because the bike could be moved easily. this was enough for people to spark up a conversation as to just wtf i was doing. something about this made people want to talk to me.
invariably i would tell my tale of the search i was on, and that i had very little money to do a ton of stuff (this was the point of the trip, not a ploy) and that i chose a moped for its low fuel costs. a lot of the time, someone would offer to pay for me to fuel up (at the time, averaging $3.75 in gas per fill up) and would often offer a meal. i would graciously decline, but i cant tell you how many times i was handed a $20 bill. in the end, i left my house with $100 in my pocket to get as far as i could, and ended up going to california and back home with $300 in hand.
as for sleep, when it came down to REALLY bad weather, i would look for small mom & pop hotels and ask for a room explaining my situation. i usually was given a room, and even at big chain hotels i could make arrangements.
but when i camped, id just pull over some place near the main road and setup. be gone early with no trace. my best campsite was in an orange grove in florida.
as a disclaimer, i made it a point never to ask for anything outrageous and wouldnt misrepresented myself in the process. i would eat at gas stations and value menus for quick stops, and grocery stores for other things.
main thing is, be polite and if you have a story to tell, dont be afraid to share!