lendusaquid,
You seem to have a problem or two. Maybe a quick jaunt to 'stuckinmuck' might get a crank without a wobble in it.
8 thou is not a lot. I would not recommend using a head gasket as a cylinder to crankcase gasket.
Simply, they are compressible, so may change like your actual head gasket, or each layer separated will be thin and flimsy. They are expensive compared to the proper gasket material. Gasket material is available in different thicknesses from about 1 thou up to 125 thou or more. You will still need an appropriate gasket thickness to set the head clearance, anyway.
Not sure what you mean by the new pistonis 'not flat'. Can you expand that a bit more?
You should only need, at most, three or four gaskets (don't know how many 'so many' might be) under the cylinder if you have a range of thicknesses to choose from. These gaskets are readily available from suppliers but a small ball-pein hammer is really all that is needed to make these gaskets, once the hole for the cylinder spigot has been cut out.
Altering the ring gap, if it is correct, will not increase lubrication to that area, it will just allow more gas leakage into the crankcase and losing some of your much-needed compression. Temperatures around that area will be quite high.
Unless you sort out why, and rectify as necessary, you may not have a long-lived engine. Longevity requires things to be running in line and minimum friction to reduce wear as far as possible. Any continued localised overheating/rubbing will eventually destroy the engine parts and, perhaps, the engine too.
If you had a bent crank, I would think that is a likely area for investigation. It may need professional treatment to straighten it to within running specs. It may even be cracked, or the main bearings damaged. Who knows. These old engines will take a lot of abuse, but I think, as far as safety is concerned, it is better to find out now, rather than after a flywheel goes into orbit.....
That is my opinion and you can take it for what it cost, but I would feel uneasy running an engine where I knew there was an underlying risk of failure. I would at least find out that it is safe and sort it out if possible.
Regards, RAB