I just wanted to check in and say thanks for all the advice. I've been reading it all. I've been very busy with finishing up my job (contract), packing up my apartment, moving things into storage, organizing the 800 Amazon shipments (bandaids/flashlights/multitools/random sh1t), stumbling around the anchor that I just bought (35 pound mantus, a little overkill but my intention is to be able to anchor safely in a nasty blow). Anyway, just packed up my apartment, which was traumatic during this heat wave, but now I'm relieved.
I got a lot of good info and thoughts here. For the record, the cockpit has two large plugs in it just below the waterline for emergency draining if for whatever reason the cockpit fills. I'm told they work good as urinals too. I have no intention of pissing over the side singlehanded, I've had some nightmares about falling overboard and I think it would most likely be game-over barring some miracle, so I'd like to avoid tempting that fate.
The boat is pretty nice equipped for singlehanding. Everything is led back to the cockpit, there is jiffy reefing on 2 out of the three reef points (I'm hoping to get the 3rd rigged this week). Chartplotter in the cockpit, with iphone + laptop with GPS as backup, plus a chartbook from here to the Canadian border. I'll sort out everything passed Canada if I end up going there. I do have a raster GPS chart of the Maritimes but I'd like to have more than that.
I did have one question though:
Learn how to back the boat upwind, downwind, cross-wind. Learn what's possible & what's difficult.
What do you mean by backing the boat? Heaving to? going into irons? Going backwards?
Anyways, keep the thoughts coming, if you like.