Generally (like, 99% of the time), new rings will not seat into worn bores. This is due to the way these bores wear when new: they are slightly egg-shaped now from overcooling, toward the 2 o'clock position on #4 and 10 o'clock position on #1 cylinders. The metals were not cured when made, which caused this warp: it happens on 100% of these engines. Now the metal IS cured and won't warp again unless you bore more than 2.0 mm, which is about how thick the cured layer is now.
I'd really suggest that you bore the cylinders at least one step (0.25mm or 0.5mm oversize, contact CruisinImage for a nice set of pistons and rings for under $150) and make the clearance 0.0006"-0.0010" (yes, that tight) for an 500/550 that will last 80k miles.