Holy cow, thank you SO much! MayaQuest Trail doesn't LOOK familiar, but I'm guessing it was the name that ended up poking my brain the most. Troggle Trouble Math DEFINITELY looks familiar from it and is the dog game I mentioned. Thank you so much!
My hopes are low, but...
-Looking for a pc game, probably from the 90s. If not DOS, it was a very early windows cd-rom title.
-I think it had "quest" in the name somewhere, but I can't quite recall.
-2d graphics
-had separate rooms you clicked to move between, sort of like a point and...
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