I completely forgot that OE/Special Prices existed. I'm pretty sure this will work quite well for what we're looking for.

I tested Alternative Price Lists as well to compare and I think it could also work. I notice that it defaults to the regular base price when there is no specified price in Alternative Price List. The only problem is that it gives us an error in OE every time we add an item that says, "Item was not found in the price list. Pricing will default from the base price list". Is there a way to disable this message?