No worries, I realize I typed these up fairly stream-of-consciousness style and my intentions aren't clear.
I'm looking for a pair of bags - one that qualifies as a 'personal item' and one that qualifies as a carry-on. One needs to be a backpack and one needs to be a roller. At least one needs to be able to fit overhead on a CRJ-200 - both fitting would be a welcome miracle. I'd prefer that the personal item be the one that rolls, as I'll be traveling with just the personal item a decent portion of the time.
The personal item size I'm looking for appears to be 16" x 14" x 7" - which appears to be nearly impossible to find with wheels. I think something like the Western Flyer or goruck Echo or GR1 would be ideal for my personal item if I have to go with a backpack, despite them all being a bit too long.