What I have seen in the past is that cyl can last a looong time if not abused. Usually a $35 seal kit will cure the leaks. Now if the oil is ran with lots of contaminates, the cyl barrel can wear and at that point a rebuild is useless. You wont know until the cyl is taken apart where you can look at it. The other thing that can ruin a cyl, or make it cost prohibited to rebuild is over pressure. Its hard to tell without a bore mic, but the barrel of the cyl can expand like a balloon being blowed up. A swelled barrel will give internal leakage with fluid bypassing the piston. New seals wont fix this and the symtems are not usually leaking oil. You could also have the bent rod problem with the rod rubbing on the side of the gland, wearing the gland out, you will get a lot of leakage around the rod shaft if that happens. My guess, and I havent seen the machine so its just a opinion, the extra pressure needed to bust that live oak, probably bent/bowed the rod as it was trying to push thru the wood. Only fix is a new rod. If this is the case, the $250 new cyl starts to look like a bargain.