Great lineage! Dave Keran is a genius, I've more or less copied his under-cuddy "tree" for line handling + stiffening the hull. Looks cool too...
Don't cut your mast (I expounded on why not in another post), if nothing else to stay "true" to the lineage.
As for your learning experiences with the boom, most sailors learn how it's called via a nasty crack to the forehead (I still have a scar, 50 years later!). So consider yourself lucky to just learn via diving

Reminds me of when I "learned" how important a retaining nut is.. the one at the top of the rudder post on my old quarter-tonner. Cost me $500 to get a professional diver to retrieve it out of the Delaware River, he found it by touch since the water is 0 viz with 4 knots current!
As for self-bailing, Ye Ol' Cut-down Milk Jug is all you need, if that. We're not racing, so a few gallons sloshing around the bilges is no big deal. Anyway, I've not yet shipped enough water to really care about bailing it out, it's mostly spray. The one time that I dipped the rail enough to ship water into the cockpit was on purpose (let's see how far we can safely heel) and resulted in a maybe 10 gallons coming aboard, a few scoops of the bucket to clear it out. I hate the entire concept of auto-bailers anyhow, it's extra holes in your hull. Very nice in theory, downright shitty when they get clogged (With all due respect to Mr Elvstrom). Good for racing, where a few extra pounds matter and you're doing constant maintenance between races anyhow.
Roller-furling is the devil's handiwork as well. Yes, I'm very opinionated and overall negative

. Rig yourself some slab (aka jiffy) reefing, it's not hard if you have the right cringles in your leach and luff. Reeflines themselves (the short bunting lines) are nice to have but not absolutely necessary. You can get teh cringles (holes) put in by any decent sailmaker, make sure to ask them to sew in some re-enforcement tape as well.