It should - and usually does. It always seems like some oil gets caught up in nooks and crannies... and in oil lines and/or filter. For example, in what I mentioned above, even though there was only a small difference in what I sucked out vs drained out, the amount that had to go back in to make it read full on the stick was (if memory serves) still about 3/4 or so quart less than spec (this was a small block).From what I understand the dip stick tube runs to the bottom of the oil pan and is angle cut just before the bottom of the pan.
I know it's probably difficult, but I would try and get to your oil plug and drain. This way you know exactly what's going on. Maybe find a skinny 14-year old that wants to make $20.
FYI, you could replace your oil plug with that remote hose drain kit.