Got the gauge set, here are some updates.
Started based on vehicle ambient temperature sensor reading 80F. With system off, the the high and low side pressures were very close. Both were within a few PSI of each other, around 75 PSI.
With the system on, max cool set on AC and engine at idle, and given about 5 minutes or so of trying to run AC saw the following readings from first image - LOW 30 PSI, HIGH 20 PSI. Following the table in the instructions added refrigerant until the low side was a little at 60PSI (accidentally went a bit high, was aiming for 55).
After the engine warmed and after finished adding refrigerant, was reading LOW 100 PSI, HIGH 100 PSI, which seemed reasonable to me given the 80F ambient plus engine heat. Wish I'd have measured the temp near the engine. At this point, the compressor was repeatedly trying to run for several seconds then stopping. I've attached a video of this, you'll see the pressures drop down when this happens. Video: https://streamable.com/7kitvx
Still suspecting the high side pressure sensor, I measured the signal voltage on the center conductor of the sensor. At 100PSI was reading 3.97V, when the compressor tried to run this voltage quickly jumped up to 4.5 and climbed to 4.9 before the compressor stopped trying to run. I'm confused as to why the reading would increase despite the gauge pressure dropping. Regardless, the voltage readings seem way high for a 0-5V sensor and the pressure ranges involved. I've been having trouble finding concrete information on what the range of that sensor is from Subaru manuals, but I found a general guide for this type of compressor that says the general range should be 0-5V, 0-500PSI ( GUIDE HERE, PDF ). Makes perfect sense to me that the controller would shut off of the compressor with a reading of near 5V on that sensor since that should mean the pressure is very high.
I am going to keep researching that part to see what else I can find, please let me know if I've made any errors in my troubleshooting so far.