Been a few crazy weeks of travel and work, but I have managed to work a few small things.
I ended up ordering a new shift and e-brake boot for the car. This triggered me to also order the shift boot bracket to replace the broken plastic one in the car now. Since I was already ordering from Rodney I went ahead and bought the shim for my getreg dipstick rather than spend the time reworking a penny.
Today I went ahead and installed the shim today and now the plug is tight and will keep water from making a second appearence in my tranny.
Also took the time to try and diagnose my low voltage at the gauge issue. At idle I am seeing 12.95v. I know it should be sitting closer to 13.6v so I will have to dig deeper into if it is a ground issue, the alternator, or the odd ball of the starter robbing it away. The real worry is that the car starts fine while cold, but seems increadibly slow cranking when it is hot from running. So now I need to get that sorted as well as the AC.