I thought I'd report back since I completed the rebuild today. I found it very helpful to have a bucket of zip-ties next to me, and the little air spraying attachement for my compressor with the rubber conical tip. All I had to do was zip tie 3 of the pistons in place, then blow air into the caliper to move the loose one out, carefully positioning a rag to catch it. I found it helpful to blow air at the hole to keep the pressure low and the piston movement slow.
On my right side caliper, everything was completely fine. I still yanked out all the rubber and replaced it anyway.
On the left side, two of the dust seals were missing pieces and starting to come apart. One of the dust seals was badly deformed, and that piston really didn't want to move at all. I'm pretty sure it wasn't helping me stop at all. Getting it out required me to move it a hair with the compressor, push it back in with a clamp, spray lube, swear, and repeat until it popped out. You could see where the dust seal had been sucked up alongside the piston and gotten stuck.
While I'm sure I could've gotten away with not doing this for a while longer, it wasn't all that expensive and certainl wasn't all that hard to do. I'm going to look at doing the rear shortly as well.