There’s a couple threads here that discuss some of what you’re asking. However you haven’t given enough data to get accurate feedback:
Type of wood/fence material (rail makes me think vinyl but could be wood)
Both sides?
Are you prepping and painting or just painting?
This thread had decent info in it relating to your questions Someone please help me price this huge 3,250 sq/ft fence job
Also posting pics would help with feedback.
