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Well I guess no one has replaced their expansion valve!
After using some gages and some help from a friend I believe we had identified the low side and high side wrong. We guessed based on the color of the cap. Looks like when the previous owner had the AC converted the repair shop put the wrong colors caps on. The low end is down by the compressor and should have the blue cap. The high side shown in the picture should be red!
Finally I just needed more refrigerant to get going again, though i probably have a leak somewhere. Placed some dye in the system so we see how long it lasts. For now it's blowing cold!