Maybe it should delete the outfits before caching them? I had an issue once where the previous time I had run it, I was a Pastamancer with a staff, and the next time, I was something else, and it couldn't cache them because I couldn't equip the staff (I just manually deleted the outfit and it worked just fine)
It should already be avoiding crashing in that case. At least that's the way I coded it last time I checked, but if it's still doing that then I need to look at it some more. When was it you tried this?
Passed outfit (MP Regen) contains less than 3 items. Please recheck your inventory.
Do you get any output at all? Make sure your zlib verbosity is 3 or higher (type "zlib verbosity" into the CLI to check) to get some useful info out of it.
Putting on outfit: MP Regen
Outfit "MP Regen" cannot be equipped because you are unable to use chefstaves.
Maximizing...
17934 combinations checked, best score 108.5
Putting on special sauce glove...
Equipment changed.
Putting on sponge helmet...
Equipment changed.
Wielding The Necbromancer's Wizard Staff...
Equipment changed.
Holding Operation Patriot Shield...
Equipment changed.
Putting on snailmail hauberk...
Equipment changed.
Putting on square sponge pants...
Equipment changed.
Putting on hardened slime belt...
Equipment changed.
Putting on velcro boots...
Equipment changed.
Saving outfit: MP Regen
Outfit saved