100% believe that a smile and a skill will set you so far apart from the average guy or gal holding a sign, as well as not looking like a fucking crackhead.
You don't have to know how to play, also; sometimes, when I was creatively sapped but needed to keep flying, I would just bar 3rd fret to 5th fret back and forth (so ez, you literally just hold down all the strings, or if lazy just the bottom string) and strum rhythmically.
I'll second this notion. Having a skill of any kind, a hustle, or things to sell will get you everything you need, and anywhere you want to go.
When i first set out hitching for the first time, I got a part time job to buy a Martin Backpacker guitar, without knowing anything about playing. I spent all those long hours on off-ramps, and miles (and miles....and miles...) of walking learning to play the thing. It made me all the cash I needed, and then some. People offered to buy my guitar, because of how unique the look of that thing is.
I never needed to fly a sign until things got real rough in Eureka, CA in pouring rain for days on end. Ill never forget the amount of shame and embarrassment I felt at that Taco Bell drive-thru line....but im over it now. You eventually figure out that there is not shame in flying a sign or spanging or dumpstering if you are in need. I am kinda ashamed of myself for ever thinking it was ever 'bad' to do that in the first place.
I'm now a confident busker, and usually always carry an instrument on me when traveling, even if I have a ton of cash to make the trip. If nothing else, its something to do when waiting on trains.
TLDR: find a skill, play an instrument, or sell stuff to make money. I would recommend at least $10/20 a day depending on if you like to drink/smoke/ect regularly. Dont ever run out of money completely....because you know the universe will make that the day you are out of food and water in a shitty conservative small town with no way out.