Welcome to iboats. Take a look at the Naden rebuild thread in my signature below. I recently completed a restoration like yours.
First, only remove all the paint if you really have to stripping a boat isn't much fun. If you have original factory paint that is in good shape, an easier job will be to simply sand it down with 80, 120, then 150 or 220 grit. The purpose is to feather out the paint, and roughen the surface to accept new paint. You then clean throughly, then spot prime with self-etching primer any bare aluminum, then do one or more primer coats, followed by your finish coats.
If you either want or need to remove the paint, stripper works - but try the plastic wrap trick (putting plastic wrap over the wet paint stripper) - it goes much faster. When the stripper is open to the air, the solvent evaporates fairly quickly.
After I did both paint stripper and wire wheeling, I preferred wire wheeling - wear goggles. Be careful on rivet heads not to grind them down, and don't try to get every speck of paint around the rivets. If you do, you'll grind away the rivets.
Once stripping is done, do a leak test on your boat by filling it to the water line. Rebuck or replace any leaking rivets before you do the Gluvit. You'll need to clean the boat before putting down Gluvit. Follow the surface prep instructions on the Gluvit website.
As for Gluvit - you will paint on the inside only, on the rivet heads and seams. No point painting the entire inside of the boat. I don't recall if I bought the gallon or quart kit for my 16' boat, but I'm sure its on my rebuild thread somewhere. You'll need about the same. After Gluviting you boat, go back over the inside of your boat, away from the rivets, with a wire wheel, to reduce or eliminate any Gluvit runs. Be aware that the areas you Gluvit will be visible, under the top coat.
After all the prep work, wipe the boat out thoroughly with a degreaser, clean it thoroughly with soap and water, then rinse thoroughly, then spot prime any bare aluminum with a self etching or zc primer, then prime the entire boat, then repaint.
As for painting, you can absolutely roll the boat if you want to - lots have....but after all the work you do, it won't be as good a finish as you can get by spraying. Other options are to buy multiple spray bombs (that is how I did my boat, inside and out, with self-etching primer). That's also how jasoutside did his Islander, with great results. Personally, for priming and painting, I recommend picking up a HLVP gun, and learning to use it. It's not that hard, and I hadn't used one before I did my boat. Yes - Rustoleum is good to use, but you'll want to thin it. I also recommend adding a hardener. I was never totally happy with how hard my paint was on the boat once I finished it. Make sure you strain the paint, and chuck out the internal paint filter inside the gun.
In terms of missing anything - just check things like the quality of your transom. If the transom is old / beginning to go - replace it at the outset. If your main objective is to have a non-leaking boat, then a much shorter job will be to rebuck or replace the leaking rivets at the outset.
Best of luck, and post some picks of your boat before and after - it's nice to be able to look back on the work you have done.
