This makes the most sense to me. I couldn't mentally picture how it would be leaking, but still hold a load. The 1 good cylinder is doing all of the work (and holding) and the pressure bypasses in the bad cylinder and equalizes in both. I can at least kind of picture it now. There are no external leaks at all on the tractor, just FYI.
I did a quick test to see how long the loader holds up with no load on it. It drops 4 inches every 10 minutes, 2 ft per hour.
I'll pull one of the cylinders and do some testing. Rebuild kits are only about $50 / side so even just rebuilding both of them wouldn't cost a fortune.
What about disconnecting one of the cylinders at a time and capping the lines so the other cylinder does all the work. The "bad" cylinder should show the symptoms and the "good" one should be completely normal.
Thoughts?