There once was a magical website called Digihitch that taught me everything I know about hitching.
I was hoping some of you might have some tips, considerations, ideas for signs, suggested gear to bring, etc.
1. People are going to laugh at me, but what you wear can make the difference between waiting 6 hours, or thirty minutes.
Wearing clean clothes that don't make you look like you spent the night in your own piss gets you rides. If you look like an average guy, in your nice clean clothes, and not like a Satanist on a murder spree (I KNOW THAT ISN'T WHAT SATANISM IS ABOUT), you'll cut down on ride times. Make every effort to look clean and fresh and it will pay off. If what you wear is more important to you than fast ride times, though, and it is alright if it is, then feel free wear what you will. Someone will always pick you up. You just might be waiting a while.
2. keep your hair, nails, and beard trimmed.
Same thing as what you wear, you look like a bum, no one wants you in there car. Again, if you prefer to have long hair, a beard, and dragon lady nails, go for it, thats awesome, you just wait longer.
3. LOOK EM IN THE EYES AND Smile.
I cannot count the number of times some nice old couple or woman stopped for me, saying "I never pick up hitch hikers, but you look so nice!" Why do I look nice? Because I smile (and because of 1 and 2). Smiling tells people that you are happy and fun, and they WANT to give rides to happy and fun people, because THEY want to be happy and have fun.
4. Choose a straight on-ramp.
A straight on ramp (one with no curve in it) gives lots of time for cars that see you to decide they want to stop for that nice, clean shaven, smiling young man with nice hair and nails who is having so much fun and is so nice! I like to stand just past the signs that say "No pedestrians or motor vehicles below X horse power or whatever." Gives people time to see you, time to stop, and something to sort of jump behind when an asshole throws things at you or tries to run you over.
5. Ask your ride where they are going before you get in, gives you time to study them, their car, and get a feel for them. If your gut tells you no, then just don't go.
6. Talk to your ride and entertain them with stories. Make them up if you have to.
Your ride picked you up because A) they want someone to complain to. or B) They are bored and want to hear a story. Oblige them and they are much more likely to kick down some food, money, or even a place to crash. But never ask them for these things. They are already giving you a ride. They owe you nothing.
As for signs, I always liked "Will not Stab you" in huge letters. That way the driver can make jokes like "You won't stab me, eh? What about posion?"
"Where are we going?" Is another one I like to use. I stay away from directional or begging signs when trying for a ride. They take the fun out of it and you get boring pity rides.
As for busking. Bring the damn mandolin, but 100$ should be enough if you know how to work it right. If you don't be prepared to play or dumpster score.
Bring a map (A good one, you cheap bastard), A sleeping bag, Three sets of clothes. Music. Sharpies. A book. Truck stop guide. Deodorant and tooth paste (duh). Fallback food. (Peanut butter, honey, and tortilla shells works awesome). I like to bring mosquito spray, but that is me. Baby wipes also help to keep you from looking like a shit pile, and stuffing laundry sheets between your clothes can help with the smell. Bring rope and a tarp for a makeshift tent. Rope is incredibly useful. Rope. ROPE. ROPE.
Take it slow. I rushed my first big hitch trip and it was hell. See the sights, take naps under a shade tree when the mood stirkes you, ask your rides to let you out halfway if you see something cool. Don't spend the whole trip in a semi. Treat the whole adventure like a game and it will be fun.
Don't worry about places to sleep. Generally no one fucks with you.
DISCLAIMER: I wrote a LOT about appearance in this post. I understand that some people take pride in their dreads and patches and this is great. You don't have to look like a 9-5er to hitch. It just helps.
I HOPE THIS WAS USEFUL.