After some testing of both options I went with the shop interface rather than a conditional check pyramid.
This works for most things that grant the 8 basic stats, however a lot of stats, like all the bonuses that the item in the image gives like Crit Chance or HP Regen, don't show up in the shop preview and there's not enough description space to list everything out. It's a trade off that works better than trying to list everything out in text form which, while thematically correct for the style of game, leads to far more menu screens and a lot more annoyances for someone that just wants to quickly grab something. I'll continue to tinker with it and see if I can adjust the description pane a bit to allow for listing out more, but for now this is how the system is going to work.
At this point all I have left are the 5 challenge bosses and the main testing run through. I'm going to do the run through first to see about what power level the bosses need to be at.