Sleep: My favorite places are rooftops, national parks, cemeteries, hostels, local's houses (couchsurfing.org), abandoned buildings... pretty much anywhere if you leave before the world wakes up. In cities it's nice to find cardboard to put under your sleeping bag so your not on straight up cement. In the country, finding places to sleep is pretty easy. Just head off into the woods a bit. People don't like people on their property though so be careful.
Another really good option is sleeping in the daytime in the park, because people are a lot less likely to mess with you.
Missions/shelters are less desirable, due to a few reasons: possibility of theft, lice (and other similar things), chance of being followed out and hurt, proselytizing, separating of families.
Places not to sleep: Parking garages, out in the open.
Warmth: Most hobos just layer up like crazy, but a fire is mighty nice.
Eat: Best information ever received. "A closed mouth is never fed." Talking to people can lead to all sorts of amazing things like food, a bed, a shower, whatever. If that doesn't pan out though, there are other options.
Food not Bombs on Saturdays in some cities, typically round 5.
Dumpster diving (Going to the D-mart) is actually not that bad. It can even be fun if you do it with friends. Best places to dumpster are pizza places, bakeries, and bulk food stores. Fast food places are okay, if necessary. Places like Walmart usually have compactors, so no luck there.
Another option, one of which I don't support, is theft, or Product Liberation. Stealing from Corporations is more acceptable than small stores or individuals, but if you get caught, they don't play around. Be careful.
I have taken some fruit and vegetables from huge farm institutions before. In Judaic law, the poor and destitute were allowed to eat from the leftover crops. It's in the bible. For real. (RELIGIOUS ALERT) Still, I figure God will provide if you walk in his light without doubt.
Missions/Shelters/Churches often provide food for homeless in cities with big homeless populations. This is sort of exploitive, but your call.
Transpo: Hitch hiking is the most viable option here, in my opinion. It's really pretty easy. Just stick your thumb out and walk backwards along the road when cars pass. Signs work too, like "Please" or "California". You might wait awhile, but rides always come through eventually.
Don't jump in the car right away. If you get a bad feeling, make up an excuse and walk away. You don't have to accept a ride. Awkwardness is better than death. Trust your instincts. PRetty much any badness can be deterred by more than one person or a knife and bad rides are not common at all, so don't not travel because of that.
Soliciting rides at gas stations works really well too.
Bikes are awesome, but you have to take care of them, i.e., fixing, maintenance, making sure nobody steals it. It's a bit of a burden.
Trains are sort of the epitome of hobo'in but I suggest not trying to hop a freight unless you have someone experienced with you.
Drink: Water is pretty much everywhere. Just carry a bottle to fill at places you rest at.
Hygiene and stuff: I use public restrooms to brush my teeth and stuff. Sometimes you get weird looks, but pride is an enemy anyways. Showers are kinda rare. but you can use sinks to wash your hair and just sorta dab around with a washcloth.
Fun: Free activities are all over! Free movies, concerts, festivals (If you're a vendor or a volunteer), national parks, museums, playgrounds and more. Also, it's not hard to make one's own fun, especially with the whole world at your disposal. Talk to people. Throw rocks at things, race, play ball, explore, fight the power, read, sing, whatever.
Communication: Library computers are free. You can usually get a visitors card or they'll just let you use them willy nilly. WILL-Y NILL-Y. You can borrow cell phones or just take your own with a pre-paid plan. I don't know about Obama phones, but I think they're free for if you got welfare, maybe. Pay phones are kinda rare these days, but not non-existant.
Clothes: Thrift stores are good, as are there dumpsters. Salvation army is my favorite. Garage sales are all over in the summer. Make a little sewing kit with some black thread and a pin to fix minor tears/button rips.
Learning: Libraries are a wealth of info, as are book stores (B&N, for example) They also provide a nice calm atmosphere. Read, read, read. You'll never have more time to read, and put your reading into practice.
You can also attend free lectures and participate in big lecture hall college classes, since those classes are impersonal. Just get a class schedule and stick around for a bit.
Some punk/anarcho communities offer free classes/free schools to teach things like bike maintenance, organic gardening, and organizing.
Health: It would be a good idea to have a small first aid kit with anti-septic, bandages, anti-biotic ointment, pain reliever, etc. Small cuts and bruises are pretty inevitable and harmless, but an infection can ruin your day.
Money?: If you need money in an emergency, there are options for that too. Craigslist is good if you're looking for work as is asking people. You could busk, or just pan handle with a cute sign. Recycling cans is good, specially in Michigan. You can sell blood and other fluids. Often people just give you money if you look destitute enough.
Safety: Travel in at least a pair if at all possible and don't draw too much attention to yourself. Most people are good, though.
Bibliography: Vagabond101, Survival Guide to Homelessness, Stealthisbook, stealthiswiki (https://dl.dropbox.com/u/64088059/Steal%20this%20Wiki/wiki.stealthiswiki.org/wiki/Table_of_Contents.html), Hobo Handbook, Evasion, Food not Bombs, counter-culture, Freegan.info, survival guides, homeless people everywhere, friends, family.
Interesting stuff. Miss you!
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