It really depends on how much you want to spend & how you want it to look when you are done. I used to do body & paint work at a collision shop & have painted cars outside(at home) before that came out fine with some color sanding & buffing. You can also make a terrible mess doing it that way and can get in trouble with the EPA.(I didn't have to worry about that 25 yrs ago)
The paints of today are a lot better AND a lot more dangerous. You can use enamel which is cheaper but won't last as long. I just bought 1 & 1/2 gallons of original color urethane (Sikkins)with the reducer & hardner for my truck for $160.00. I am going to have a guy I know at a body shop paint it for me. I don't have the proper equipment at home AND without the proper resporator the isocianates(?) in it can kill you.
Check with a couple local body shops & ask where they buy their paint from. Go to the local paint dealer & ask them what you need for supplies & safety equipment. If you ask a body shop how much to paint your truck they probably are going to start around $3000 & up. You get what you pay for. If you have a SAFE place to paint it, maybe a booth someone lets you use, would try it myself.

1957 Chevrolet 1/2-ton Stepside LB in the Gallery
My Photobucket shots

The person who has nothing for which he is willing to fight, nothing which is more important than his own personal safety, is a miserable creature and has no chance of being free unless made and kept so by the exertions of better men than himself." - John Stuart Mill (1806 - 1873)