Update! I've got working AC again.
I installed the new drier, and a new refrigerant pressure switch. Maybe that was unnecessary, but I felt like I'd rather have a fresh drier, and not a 19-year-old switch after getting to this point.
This is the AC tool kit I bought including gauges and vacuum pump:
Amazon.com: Kozyvacu AUTO AC Repair Complete Tool Kit with 1-Stage 3.5 CFM Vacuum Pump, Manifold Gauge Set, Hoses and its Acccessories … (KZTA35011): Automotive
I don't have anything to compare it to, but the gauges seemed to work like they are supposed to. It was in the 90 degree range in my garage. With 26 oz of refrigerant, I ended up around 45 PSI on the low side and around 230 PSI on the high. To be honest, I was really focused on watching refrigerant flow and weighing the can toward the end, so my memory might be off.
The vacuum pump worked just fine. To start, it pulled vacuum down to 29-30" within a couple minutes. It was quieter than I expected , compared to the videos I had watched. After the first pull to full vacuum, I closed the high and low side knobs to let it sit for 10-15 minutes to check for leaks. It turned out I had to run into work for a meeting that went really long, so it sat for over 2 hours and didn't seem to drop at all. I turned the pump back on and let it run for an hour to get any remaining air or moisture out. After closing the low and high knobs, I removed the vacuum pump. I suppose I could have saved myself some money if I had done the Autozone loaner pump, but I don't regret my decision. Running back and forth to AZ, making sure it's available, and maybe having to do that again in the future were potential hassles I'm glad I avoided.
When I got to the recharging stage, I went really slow to make sure I was following all instructions, checking for leaks, purging lines, etc.
My biggest struggle doing this project was the can tap. I already had 2 self-sealing cans sitting on my shelf, but no tap. The tap that came with the above kit was the older puncture type. I bought a new tap on Amazon made for the self-sealing cans, but I could not screw it on a can without refrigerant leaking before it would seal. I went to Autozone and bought another tap made for self-sealing cans, and it went on just fine. However, the outlet was a larger flare fitting than my hose, so I couldn't use it either. My third attempt was the little blue plastic adapter that screws on the self-sealing can and allows you to use the puncture type tap. This wasn't perfect, as there was a bit of a leak screwing the tap to the adapter, but it was 1-2 seconds, and only with one of the cans.
My second biggest struggle was self inflicted. I opened up the first can to start charging the system with the car off. One of 50's Kid's videos did it this way rather than starting the car first, and it seemed a wise way to go in case there were any major leaks, I'd be able to hear them without the car running. That went fine and the system took some refrigerant and then equalized so it wasn't pulling any more in. I started the car and waited for the compressor to kick on, but it didn't. After a minute of panic wondering what I screwed up and if I'd have to tear everything apart and start over, I took a breath and wondered if I had reinserted the wire connector for the AC clutch. I had not. I reconnected it and started the car, and the AC compressor immediately kicked on.
The first can went in just fine with the compressor finally running. An 18 oz can, which was 17 oz of refrigerant and 1 oz of oil. Before this repair, it looked like I had leaked about an oz of oil with the bad o ring leak, so went with it. The second can was 12 oz of refrigerant, so I put that on a scale before opening the tap, and kept remeasuring until it was 9 oz lighter.
I took the car for a short drive in the 100 degree plus weather in July in sunny Phoenix, Arizona, and everything seems to be working great again.
It's not a super difficult job, but I'll say it was nerve racking at times following the steps and making sure I did them in the right order. I was also a little afraid I'd screw something up and have a can or hose explode. I'm guessing if you follow the instructions, there's a very low probability of that, so it most likely was just anxiety doing something new that I don't deeply understand.
Overall, I'm glad I decided to purchase the gauges and vacuum pump, and do the work myself. I learned something new, and now I feel way more confident that if I have a problem again with the AC in this car or any other, I can tackle it myself with enough time and patience.