Okay, time for me to chime in. I think you are way too old to be attempting this build and should instead send that roller to me ASAP. If that won't work for you please put me in your will.
I can go from right side shift to left easily, only takes a minute or a mile and it becomes second nature. Might be easy for me because I've done it so much and I can see where you can mess up if you're not paying attention.
I think the first electric start XLH came out in 67 and uses the same motor mounts so it should go in that frame. That roller is exactly what I am looking for to put a big Sputhe motor like my 1327cc in it.
You're never too old to ride as long as you think you can. This is my buddy Jim, he's got a few years on you;
He rides this nitrous injected Sportster: