$1000 is probably doable if you can find someone who has the equipment to shoot if for you for cheap (less than $500). Depending on Color and paint system, you are probably looking at about $500 just for the paint, primer, reducer, converter, etc... If you do awlgrip, here is how I would do it:
sand existing paint with 150 grit
Shoot 1 coat of 545 epoxy primer
fill any dings, etc... with awlfair
sand with 150
shoot 1 coat of high build primer
longboard and fair
shoot 1 coat of 545
lightly sand
shoot 1st coat of finish
lightly sand
shoot intermediate topcoat
lightly sand
shoot final coat.
Some guys then wet sand and then shoot a clear coat on top.

Each step is not alot of time, but there are alot of steps. If you add up the materials needed to do this, it is close to $500 (could be more depending on colors). This is how we did mine, but did not do the high build (wish I had). The hard part is getting the right conditions (when the painter is available) to shoot the finish coats.

Good Luck!!