I know this was posted before but I can't find it. I would like to paint a maple (pineapple post) head and footboard for a new place. Guest room, so not daily use. Do I have to strip the factory finish, or can I just prime it after cleaning? Would flat or glossy work best for recoat? Or would a wood stain be better?

 

Assuming the headboard is real wood not veneered etc then it probably has a sealer of some sort.Likely that would be polyurethane so it's possible a tinted poly would work but stain itself would not because it could not penetrate.You'd have to test the poly on an out of the way spot to check for compatibility to the existing finish.

If you paint,scrub down with mineral spirits,prime with an oil primer and top coat with an enamel either oil or waterbourne.I'd stick with at least semi gloss or high gloss for easy cleaning.Scuff sand the finish to help with bonding though the primer will bond anyway.