First of all, realize that you can do this. It isn't difficult, but it is painstaking and time consuming. Recognize that the effort is worth it, especially if you like saving a LOT of money - as much as $10,000 or more for a boat of 35 feet. A professionally painted job is very expensive, and when you've completed your own boat, you'll know exactly why that is.
Next, realize that your job will not be perfect. If you follow the instructions given you by the paint manufacturer, watch the videos, don't flinch at the effort required, take your time, have patience when it rains or is too humid/hot/cold or there's a hurricane in the forecast (it happens!) or an earthquake (they both happened to me!) and you can't paint, you'll end up with a great looking job that, when your boat is on the water, will look spectacular as close as 5 or 10 feet away. The only person who will know of the paint runs, the little nick you didn't fill properly, the small section of orange peel - will be you.
The great news is that once your boat is in the water, the ever changing reflections from the water's surface will mask minor imperfections, making your boat (and you!) look better than it (and you!) actually is (are!).
I've seen lots of boats where the owner scrimped on his labour while prepping the boat, and it shows. If you take six weekends to paint the boat, at least five of those should be prep work - removing hardware, dewaxing, sanding, filling nicks and dings, sanding, fairing, sanding, priming, sanding.....all of this just to get to putting the first coat of finish on. And then you have to sand that too!
There is no other job an amateur can do on a boat that will return as much in equity as painting your boat. A fresh paint job will add thousands to the value of your boat and if it only cost you $1000 in materials, you're way ahead.
Do I actually need to paint my boat?
Maybe you don't. Before you paint your boat, take a good look at the gelcoat and determine its condition. It may be possible to bring it back to life with rubbing compound and a buffer. Or, you might have to be a bit more aggressive and take some sandpaper to it, and then compound and wax it. Or you might try one of the various 'hull restorers' such as Poli Glow.
But if you've got scratches, dings, general wear and chalkiness, you're probably into a paint job. Done right, you won't have to bother with an annual reapplication as with a hull restorer, or re-compounding and waxing each spring - although you would be wise to use a good quality wax every season as part of your regular upkeep to protect against UV degradation.
And of course, if you're wanting to change the colour of your boat....
