You can get terrific results tipping and rolling, but the boat needs to be properly prepared. Have you ever painted anything?
Which boat size? Do you intend to paint the topside, sides, and bottom?
Purchase excellent paint. I can't estimate that because I don't know the size of the boat.
A sander, sandpaper, scraper, foam rollers (foam can assist eliminate bubbles and require less tipping), brush, roller, paint tray, rags, acetone, soap, access to water, painters tape, and sometimes paper are required.
Do you need to patch up any holes and cracks? If so, you will require some filler and perhaps a tool like to a Dremel to assist in sanding the spots.
A wrench, sockets, and potentially allen keys and t-star screwdrivers are required.
Preparation is key. Consider just painting the transom and seeing how it turns out. If you work every day, it will probably take a week to complete. This is so that the paint can cure for about a day between coats. Sanding could take a day, taping another, and painting could take three days.