After a lot of googling I think the only thing I haven't tried is a tile bit. Any suggestions?
Plasma cutter? CNC waterknife? LOL
Seriously though, I had to cut 13 holes (some square to capture carriage bolts) in 50 sheets of metal. CNC plasma cutter ate it for breakfast, though I would've rather used a waterknife. Less rework.
masonry bits, and even regular wood drill bits
running my drill press on the lowest setting
There's your trouble right there. You're blind guessing.
For any given metal, there is one correct/ideal feed (the depth of cut) and speed (the linear rate of cutter movement through the material). If you're in the ballpark, fine. If you're not near, well, you found out.
Machinery's Handbook (or other resource) will have correct feeds & speeds for your material. In drills that translates into RPM (for a drill size) and plunge rate. Once you have the drill at the RPM the book actually says for that metal and bit, an attentive operator has a reasonable chance at finding the correct plunge rate/pressure, just by noting what force makes it cut "like butter" vs fail to cut.
But work fast. If you're "not cutting" for even a second, you are "work-hardening" the material. Too much of that and you're done. You'll need to find another spot, find another part, switch to waterknife, or do something thermally to remove the work hardening. But the latter may destroy the properties of the metal.
That's why you kept destroying better and better bits, you kept trying to re-drill the same place you'd already work-hardened.
Harper's rule of cutting metal: If you're not cutting, you're not cutting. STOP!!!
Once you get it dialed in, it's sheer pleasure. You're banging holes out very fast, using little oil, the bits aren't dulling and aren't even getting warm. (yes, all the drill press' power is being turned into heat, but the long chips like spaghetti noodles are carrying it away). That's your happy place.