Thanks for your suggestions!
Mariush, I intended to use LM7805 and LM7812 regulators with this particular design but had to change them out last minute because the footprints that came with KiCAD didn't map the pins out correctly so I had to find some equivalents and didn't even think twice about it otherwise. I probably wouldn't have noticed my mistake if you hadn't have pointed that out
I will look into adding some caps in then. I also meant to lay out the board with both of the regulators as TO-220 packages, I wall have to go back and double check to see if I got that right. As for the -12v rail, I sort of skipped over it in anticipation of finishing everything else first and then forgot about it.
ChristofferB, My intention in shorting those pins was to allow full read/write capability when the 8088 signaled it was accessing an IO address, but then only have it respond when the A0 line on the chip was held high. I probably have that way wrong, since looking at the datasheet I now see that A0 is used to check the status of the 8088 chip when issuing an interrupt. Do I have that right or am I completely misunderstanding the datasheet?
I'll look into using the 74LS138, It should help clean up some of the messy jellybean logic.
Again, the intention of shorting IO/M to RD was to allow both conditions to turn on the CS2 line on the UART, but I now see what I was doing wrong. I will definitely fix that so I don't blow a precious 8088 during testing.
Thanks for all of your suggestions!