Upgrade Planners can bypass the Quality Requirement.

Setup: Create upgrade planner (Ctrl-U), add to inventory or quickbar, right click to open, add an Assembly Machine (Any Tier) to 'From'.
The 'To' selector now allows upgrade to 10 T2 and T3 Assembly Machines (5 each), with the upgraded module slots, without the higher Quality requirement.

Another (smaller) quirk found:
Non-common quality Assembly Machines cannot be selected with the upgrade planner.

Yep. Both of these are a side-effect of the gimmick method used to fake the higher-quality stuff.

The first one is probably fixable? Depends very heavily on if there's a on_upgrade_entity or whatever.

The second one is only fixable if I un-hide the new entities, but that causes problems with mod integrations (to be specific: infinite quality tiers, you'll be scrolling through 255 times the number of assembling machines - in SA that's AM1, AM2, AM3, EM plant, biochamber, foundry, and cryoplant.)