It depended on how fast I moved the flywheel. If I did it with any speed (pulling somewhat slowly on the pull rope), the vacuum level would raise and lower as you would expect, but then always return to a little more than 7 in hg. If I moved it slowly (just moving it with my finger), the value would fluctuate slightly but again always return to 7 in hg. If I ran it up to 14 in hg, and them moved the flywheel until it started to bleed down, and then ran the vacuum back up to 14, it would still blead down to 7 without moving the flywheel any.
Based on the previous quote from the repair manual, it sounds like my oil seals have reached the point of needing replaced. They may not be in terrible shape, and it may not have contributed to the issue with my piston, but if I don't deal with the problem now I'll soon be going through this entire process again as the seals continue to degrade.