The standard way of checking the rings is to perform a compression (pressure) test on all cylinders. You should do this with the engine warmed up. If one or more cylinders reads low, then you have something (worn rings, valve, head gasket, crack) that is leaking. To figure out if it's the rings, you put a teaspoon full of oil into the leaking cylinders and repeat the test. If the compression goes up after you add the oil, the leak is caused by poor ring seal.
I don't like your idea of rebuilding the engine through the bottom end. You need to measure (or feel) the bores to see if they're tapered - (more wear at the top than the bottom). If tapered, you may need over bore and oversize rings. Even if not tapered, when you replace the rimgs, you should crosshatch (diagonal hone) the cylinders to ensure good ring seal. The fastest, easiest way is to do it right the first time.