How about multiple shirt designs but they still all say 'Cruiser Gold Rush'? That way there's a little bit to go around for everybody. Heck, we can even make a shirt with a Tacoma high-centered on a pebble 
For example, if folks like the design my friend came up with, I'd put it up on a tshirt "campaign" site. Think of it as KickStarter for shirts. Would probably need a minimum order of 5 shirts @$20 to get it going. People buy their shirts directly from the site. That way nobody has to front any money and there's no extras or shortage of shirts. You can even setup campaigns for hoodies, long sleeve shirts, whatever. As long as the minimum number of orders are met to cover base costs, they'll print them.
Even if you guys come up with a different design, I'd still suggest doing this as an online order. Much easier and less hassle as they take care of everything.
Example on a hoodie
For example, if folks like the design my friend came up with, I'd put it up on a tshirt "campaign" site. Think of it as KickStarter for shirts. Would probably need a minimum order of 5 shirts @$20 to get it going. People buy their shirts directly from the site. That way nobody has to front any money and there's no extras or shortage of shirts. You can even setup campaigns for hoodies, long sleeve shirts, whatever. As long as the minimum number of orders are met to cover base costs, they'll print them.
Even if you guys come up with a different design, I'd still suggest doing this as an online order. Much easier and less hassle as they take care of everything.
Example on a hoodie

