Couple of thoughts -
See appendix D of FAR part 43 for a list of what's normally checked on a 100 hr / annual. (As you'll see, not too much can be done to see inside an engine.)
The thing I've noticed over the years with Lyccomings is that they can have great compression but very worn cam lobes / lifters.
The result is the cylinder seems fine, but essentially can't breath. So, it puts out much less power than spec.
If there has been oil analysis, check for trends in the metal - if not, what do the contents of the filter look like? (If the oil was very recently changed, there might not be much to see. Open up the filter and see, with a magnet, whether there is any amount of steel in the filter.)
One other idea would be to use an automotive type compression test. (You hook up the tester and spin the engine. (Disconnect plug leads and pull the top plugs.) The peak compression is recorded. Unlike the conventional leak-down test, the automotive test can tell you something about the condition of the intake as well.
So, the automotive test and a borescope exam would be on my short list.
Last ideas - you would probably want to make sure you had a current wobble test for the valve guides, the mags have been done within 500 hours, and the impulse coupling has been inspected.
Dan