I just did a restore on a similar boat.
Personally, I would wait till fall to paint because most paints recommend waiting 2-3 months before putting it on the water after painting.
I researched a lot of different types of marine coatings and decided to go with rustoleum. Awl grip and Interlux are probably better paints but they are 2-3 times the price.
I ordered 2 quarts of the primer and 4 quarts of the topside paint from home depot for around $125. This gave me 2 coats of prime and 3 coats of paint.
Now, I did use a sprayer but rustoleum recommends using a roll and tip method.(google it) If using a roller use a foam roller for a smooth finish.
I fixed all my cracks with a fiberglass resin kit from Lowes and then rotary sanded with 220. Wiped clean with xylene and then sprayed on my first coat of primer. I wet sanded lightly by hand with 600 between coats, the paint is self leveling but I did get some "orange peel" which the wet sanding helps. I then again wiped clean with xylene and applied the second coat of primer and repeated this process through each coat of paint. After the second coat of paint I bumped up too 1200 sandpaper but did not wet sand the final coat.
After a week the paint was still very soft but now after a few months is fairly hard.
Good luck, its a nice looking rig. If you need anymore advice feel free to contact me. I have a good method of getting the boat off the trailer to paint the bottom if that becomes and issue.