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David,
I don't agree with Larry's comment that "as long as you are not making metal, you will be fine." (Sorry Larry.) You can have failures, including catastrophic failures, with no unusual amount of metal in the oil prior to the failure.
I will let others who are mechanics comment on the rest of your message, they are more qualified than I. I will say that I have followed approximately your strategy on both my 337s (and other airplanes I have owned). The difference is that I would not have run my engines beyond about 1800 hours. As the time gets higher, the chances of a catastrophic failure get higher, and if it happens, other than the obvious safety implications, your core is worth less by a good chunk when you replace the engine. Also, I would consider very carefully the wisdom of doing more cylinder work on an engine past TBO. If it is just one cylinder, I would likely do it. But more than one, the chances are that you have to do more at the next 100 hour or annual, or you have to overhaul the engine, and then you don't get much value out of the cost of that cylinder repair (because you are replacing it at overhaul anyway).
As I say, I hope we hear from some of the mechanics on the board on this issue, and on your compression question. My previous mechanic told me that the compression question is more complicated that just a reading of 60/80 or better, or whatever. There is a Continental bulletin on this I believe, and I think it matters whether the leakage is intake or exhaust, etc. etc. But I can't remember the details...
Kevin
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