The piston seals are a (notoriously frequent) wear item, and sometimes the (fortunately replaceable) cylinders too.
I wish to clarify the above. It seems to be a generally held belief that oiled air compressor pumps (particularly the heavy, non-homeowner-oriented models), that are both a) run at the correct speed, within duty-cycle & pressure specifications, and b) maintained on a reasonable basis with air filter & oil changes (of the proper type), will likely operate trouble-free for a very very long time. In comparison, oil-free air compressor pumps have issues sooner; their operating costs are higher. Issues with receivers (tanks) are another matter (drain them frequently!).
The value of oil-free compressed air has to be judged by the end user. A slightly involved analysis can be done to determine whether requirements of the compressed air are best achieved with an oil-free pump or an oiled pump followed by some number of filtering mechanisms. A direct replacement of the OP's oil-free, 2-stage, 60-gal, upright, wheeled air-compressor looks to be $1000+ new at this time. Depending on situation specifics of course, it may be cost-effective to repair. If the oil-free air requirement is unnecessary, the decision to repair is more difficult.
I concur with the advice that diagnosis is the proper course of action; a number of leaking things could be the issue. However, my bet is on the 15 year old piston rings (and cylinders if you're mildly unlucky). If you take the shroud off, you can look into the bottom of the cylinders and see much of their walls (manually turn the motor if necessary) and I think you may be able to see some of the piston rings (and possibly a glaring issue if lucky). From that Sears link, one each of kits K-0648 & K-0650 will allow you to change both cylinders and rings. I'm familiar with the K-0650 kit, but the K-0648 kit I see on ebay has far more items.
Is the compressor louder than it was years ago? I feel like mine became quieter after replacing the cylinders & rings (a chunk of ring was missing on mine).
I believe you likely have a rebranded DeVilbiss air compressor. Do you see "AC-0782" somewhere on your unit? See here for more info:
https://www.garagejournal.com/forum...or-craftsman-devilbiss-air-compressor.482736/