In an attempt to simplify my life I had my stock 292 distributor converted to Petronix II which didn't fit well as the collar that replaces the rotor was sloppy on the shaft. So instead we pulled the original distributor and replaced it with a reman one so I could drive it from Seattle to Chicago. It worked from Seattle to the going to the sun road where the bearing on the distributor shaft wore out and made the timing suffer. We stopped in white sulphur springs and had a replacement used 1960 something distributor swapped in and it ran well enough to get us home to Chicago. Then after about 2000 mile the bearing on the Dist went bad so my question is what do I do? Another Dist? Could the cam be causing problems? Is there an oiling issue? Would a billet mad cam and electronic ignition be a better choice or will I just chew that up too?

Sounds like you've been plagued with a run of bad luck with the distributors.  While distributors will wear, they do it gradually enough that it takes many miles.  I'll suggest making sure the distributor is pre-lubed on the shaft before you install another but beyond that, it should last for tens of thousands of miles without much issue.  The only other thing I'll suggest is making sure the engine is vented and not sealed up.  A working PCV valve will go a long way in making sure excess pressure is not being created in the crankcase which in turn could be forcing premature distributor shaft failures.  This is some 'way out' thinking as sealed up or non-ventilated engines typically leak oil badly enough that they don't get driven enough to make other problems come to the forefront.

Lorena, Texas (South of Waco)