First things first, don't worry about posting or not posting as you ruminate. I think I had three or four pages of ruminations for my Smallstate thread before I ever turned a wrench on it. Thinking with your keyboard and getting responses, suggestions, and the occasional warning is a great way to learn. If people get tired of it, they can quit following your thread.
Next, I still think there's value in doing a stock-ish rebuild to cut your teeth on these motors. Maybe not with your existing Frankencases, but you have everything you need except for the cases. Do a build on a BGM 177, get comfortable with how things fit together, and get used to riding it--fast bikes take skill to not kill yourself the first time you twist the throttle (and every subsequent time, too).
I have a BGM on my SprintV cases and it GSFDyno'ed at 17HP. That's not at all shabby, but also not so fast that I can't run it with stock parts. For most folks, that's the sweet spot in the Cost-Performance-Reliability triangle. First kick start; Goes Plaid; Built with stock internals, other than replacing the 6-spring with a 7-spring (but still stock) clutch. If it wasn't in my VBB, it'd even still be autolube.
Also, assuming that Kajit hooks you up with some fresh cases, you could have the whole thing back together and running in time for New Years.
If you get a few miles on it and don't think that's enough power, you can start to plot the Beeg Motor Projyect. If it's going to be all new parts, you're looking at three or four grand to build it up, because you'll need to splash out for high end clutch, crank, gears, ignition, reed block, carb, suspension, wheels & tires, etc. For that kind of cash, you want to be sure you're going to do it right so you don't wind up blowing it up with bad timings or jetting, or getting smoked off the line by some jerk on a beat up smallframe or a couple guys who learned English from watching Howard Cosell.