I think you're better off monitoring the level with the dipstick (that's what it's for, after all), than trying to do precision drains and measuring what comes out. There's always some spillage, some oil on the sides of your measuring container, what's left in the filter, etc., which results in an inaccurate measurement of drain quantity. The dipstick, on the other hand, should give you repeatable resolution to .25 qt as long as you measure it the same way every time. (Level surface, engine off for at least 10 minutes, that kind of thing.)
Also, my experience has been that overfilled engines will get rid of the excess oil pretty quickly (unless you have something like fuel or coolant getting added). Not exactly sure why (my theory is that it has to do with the excess oil getting splashed up on the cylinder walls from below increasing the burn rate, but that's just a theory), but typically if I fill to the full mark or a bit above, the oil level will fairly quickly drop to about .5 qt below the full mark and then stay there for 3-4 thousand miles. Depends on the engine where the "happy point" is, but they all seem to have one.
Losing a quart every 5000 miles is not cause for concern re: the engine health, and certainly is not a reason to tear into the engine, as long as it stays consistent.