Dam nice guitar worth "upgrading" like you are doing, in my opinion. It will be interesting to hear about those creamery pickups.
I have a guitar with the vintage style tuners and the posts are loose and rattle in it as well. I bought a wood reamer and am going to do my own reaming the next time I put new tuners on a guitar and the holes need to be enlarged. I might put Grover mini locking tuners on this particular guitar and it will have to be reamed. These will be the type of tuners with the threaded sleeve kind of nut on top instead of the push in type.
Definitely keep us tuned in as you fix up this guitar. It's interesting.