We beach quite often and I put on one that a bit longer than recommended, so I'd agree with @Scott Danforth in post #4.
The keelguard does a great job of protecting against sand scuffs. Even better, we hit a rock ledge at our lake in Ontario (water was unusually low last year) at slow speed...
In Illinois, you have to have the plug removed and the bilge drained, ostensibly to minimize the chance of transporting invasive species (e.g., zebra mussels) from one waterway to another. I believe that would include livewells and other types of holding tanks that empty into the waterways...
PT lumber (and PT plywood) that we get is always wet and is always 2nd or 3rd grade lumber. I can do much better with exterior-grade plywood for boat work. I would never use PT stuff with fiberglass.
I like 'em. I have them on my trailer and I've not had problems with them at all. I still do maintenance on the bearings regularly, but I like the idea of the grease being somewhat under pressure to reduce the chance of water infiltration.
I do at least a couple 1600 mile round-trip journeys with the trailered boat every year, partly over highway and partly on fairly undeveloped roads.
I don't carry a hub, but I do have two sets of bearing/seals/etc. and the tools to replace them, along with two spares and a bottle jack. I also...
I've never had to tighten down the nuts to get the drive to go on all the way. I don't think you should have to crank down on the drive to get it to seat fully. It should slide right up to the bellhousing.
I have the Daytona 3 ton jack. It works great. Of course, I never work under the vehicle without jack stands, but the floor jack is well made and mine has been quite durable.
I don't think fiberglass expands much in the heat, so it's pretty unlikely your bimini isn't fitting because the fiberglass is moving.
My Sunbrella mooring cover is always a bit tight after it has been sitting for a while, but the fabric tends to relax a bit when it's being used regularly...
This happens a lot. Sometimes turning the propeller to turn the drive shaft will help. Other times, I've gone away and tried again the next day and it slid right in.
Best things to check are (a) the o-rings (light oil or very light grease is sufficient) and (b) the alignment of the coupler...