If it a wood boat then you want a very different sort of paint job than you get with a fiberglass boat. For one you do NOT want to use a two part urethane paint like Awl-Grip, Sterling or Alexseal. You want a much softer paint like a one part urethane or a traditional oil based paint like Kirby. In addition the surface prep will be very different. I base this on my experience with my 1936 wooden boat which I repaint myself. My boat is 33', but is a raised foredeck design so actually takes a bit more paint than yours. That said, you will only need about 1 to 1.5 quarts of paint per coat. You can get a very good result with either straight brushing or a roll and tip job. If you old paint is in OK condition you don't even need to prime except for any spots where wood is showing through. Two coats should do it. Here are some time numbers for painting my boat (see avatar).
Sand topsides to 220 grit - two hours per side (4 hours total)
Mask hull - 1 hour per side (2 hours total)
Apply paint - 1.5 hours per side for roll and tip, 2 hours for brushing (3-4 hours total)
Sanding between coats 1 hour per side (2 hours total)
So for two coats on my boat painting would take about 12 hours. I would use three quarts of paint total and maybe a pint of primer. In addition I use about three rolls of mashing tape.
Materials cost using Petit Easypoxy paint, 2" masking tape, foam rollers and tipping brushes and a 5 pack of 220 grit sanding disks comes to about - $155
Labor at $100/hr would be around $1,200 so say $1,350 for two coats of topsides paint. That is less than the materials cost for two part urethane and primer.
Times above are my times to do the job myself. I paint the boat every year so my times are based on 8 years experience.