Wow. All of these issues are familiar, but they usually come up one at a time.
The presumptive cause of the CB being stuck down is the slack uphaul cable slipping between the board and the side of the trunk. Did you have a bungee tightener on the uphaul to keep the slack out? If not, that's probably it. When that happened to me, I removed the CB and replaced the (now bent) cable tangs and cable. And installed the bungee to prevent it from happening again.
The sources of bilge leaks are usually:
-- poorly fitting or (ironically) over-tightened CB bolts that deform their sealing washers.
-- poorly sealed drain plug
-- deteriorating putty around the through-hull where the CB uphaul enters the cuddy
-- cracked or leaky deck plates in the cockpit
-- gaps in the hull/deck connection (but only lets water in when the boat is heeled sharply)
Right. The DS won't sail upwind without the main. Everyone has tried it. Everyone has the same experience.
Motors always die when you need them most. You didn't know that?
If one thing can catch on another it will. I have taken to taping my split rings to minimize snagging. Another classic is to snag a line on the split ring of one of the shrounds, which then pulls out, releasing the pin and causing the mast to come down.
And as long as you're serving as poster boy for all things unlucky about Day Sailers, I don't suppose you have reinforced the lip where the shrouds attach, or the forepeak where the stemhead attaches? Those are pure, under-engineered design flaws that don't happen often, but that make the news when they do.
Don't know if you are a drinker, but if you are, have a stiff one. Do some fun things on dry land, and then set about the fixes, all of which are well documented on this forum.