Thanks for the update, thinking we are going to head this direction rather than rollers. We will probably rent a larger unit, but it looks like yours was working great.
I could've bought a larger unit with hose (home owner model not that expensive, look at the ebay seller link for reman), or used my friend's large hose fed unit. But the problem is wasted paint. The hose and pump hold a lot of paint.
With this handheld unit, you can actually store paint in it over night (I did two nights once). There is no air in the bag that holds the paint, so just close the tip and leave it overnight. I did this between coats.
Sure, it takes longer to go back and fill container that holds the paint more often, but one could easily buy multiple holder assemblies to just clip on as you empty one.
I used Bluewater paint for a coat because that's what I used in the past (but they went up in price), but then I switched Woolsey yacht sheild SF (same as Pettit Ultima SR but cheaper). I put a bunch of coats on, but try to spray a coat and then let it dry overnight before spraying the next. That's why the store with it in bag is nice, no wasted paint in the lines.
Also, because I use ablative, I'm not too worried about getting a perfectly even coat all the way around. I just want to get a bunch of paint on the bottom....in my experience it wears off and smooths itself out.