Phil, glad you found something familiar to do when on the road. As far as the boat loading squarely, I had a bigger problem when loading the flatter bottomed 1801. This 2120 with the 21-degree hull slips into place much better, but the rollers still can't be submersed too deep. When in the slip I notice she lists to starboard also, but when leaving the motor tilted up, I lean it to port and that almost fully straightens things out. A 5 gallon bucket of water on port side almost full seems to square it up. I figure it's due to the helm and 2nd helm station on the starboard side. Everything else is symmetrical. Surprisingly, it's hardly noticeable when on the trailer. Definitely acceptable.
As far as paying out too much cable, the strap version of the TW9000 is supplied with 20-feet, and the cable version 30 or 40 feet, so you should be ok. There may even be some means of cable retention. The DL2500A supplied with my trailer, has a sewn loop on the drum end with a bolt through it, so running fully out is not an issue. Funny thing, when loading for the first time, I thought I had a single speed manual winch, and brought it all the way in on the "fast" speed. The Dutton-Lainson manual winch uses a quick detachable crank handle that swaps between two different shafts. I've never had that type of gear selection before. The fast mode requires 4.5 cranks per foot of webbing (full drum), and 15 cranks per foot on slow/easy mode.
I got the Expedition back today with the high-amperage power outlet installed. They used a 175-amp connector in order to accept the 4-ga cables, but installed an 80-amp breaker on the firewall. They used Anderson PowerPole connectors (SB series). I've seen these used on electric forklifts, floor scrubbers and UPS battery banks. They also supplied a matching rubber boot to cover the connector when not in use. As tough as it was for me to pay someone else to do the install, what made it worse was when I got home I noticed the contacts were barely inserted and not clicked into place in the housing shell. They had some young kid do the install. If I'm going to pay top dollar for an install, I expect it to be done better than what I would do. I struggle with this on everything that I could do myself. All in all, a nice install. I might even modify a pair of jumper cables with a matching connector on one end, for when backing up to another vehicle is the only option.
I will look forward to meeting up one day next season. Do you ever fish out at the Cape May artificial reef? I freedive & spearfish many of the wrecks out there. It should be about the same distance from your port as from mine. I head SE once I leave Cape May. You probably head more south.
P.S. Here is a factory link to show how your cable is attached to the drum. No danger of it unraveling.
https://youtu.be/t4R2awyn-IQ