After enduring a few weeks of vacuum trouble with no vacuum know-how, I finally found the problem. I just received my mity-vac in the mail and when I crawled underneath to locate the line that goes to the tranny itself and moved it, I realized it was just sitting on top of the connection and not connected to it. I was equal parts - Eureeka I fixed it! and I'm a dumbass! I drove it and it shifts like a dream. Thanks to anyone who endured my questions before. I would advise anyone to double check this line, as I looked at it before with my eyes and not my hands.
On a side note, I was going to order all new vacuum connections as mine are all dry-rotted. Does anyone know exactly how many there are? I can see 5 and one multi-connecter. I don't want to order less than I need.
Thanks.