I love your suggestions but a rebuild of the tranny is not much of an option for me. Back in the day, when I was a little younger, I would have jumped on it. I'm 65 now, and the prospect of getting the motor out and then back in to the frame is.... daunting. I should have a job this winter which might provide some funds but I am retired and there are certain restraints in cash as well as physical limitations that were not an issue when I had my last Venture back in '97. I will not be hammering on the motor anyway. Not my riding style. My priorities will be good tires and brakes, careful and thorough inspection of the drive train, re-lube all bearings and such. I will spend some time keeping the bike looking sharp. My shop is fairly complete, but I do miss my milling machine and glass bead cabinet. I might have a lathe next spring but I'm not sure it's condition yet. I have a nice tig welder for the frame issue, should it arise.
For this restoration, my approach will be....um...more sweat than cash. I guess that's the best way to put it. For example, instead of shopping around for a minty original trunk, I've glassed up the shattered lower trunk case. I did the same with the side covers. They look great. My biggest fear is age related failure of the various seals on the motor. The rubber of the brake lines, carburetor diaphragms, etc. are all at their "end of shelf life" stage. I've been wrenching on bikes for over 40 years so I've some idea what I'm doing. This is bike #20 for me. I don't imagine I'll put on more than 10K miles on it before I give up and retire from riding. I think this bike will be fine for my purposes, without a transmission rebuild. Though it would be fun...