Maybe you should look at More Hotkeys and see what he's done there. He has special Stance sets that will equip entire outfits and gear. It would be a bit of a work around that would probably require using some keys outside the Pipboy but it would do the job.
That's a pretty minor problem really, and not something I'd consider an issue worth worrying about.
So I've been playing with the new version for about an hour now and haven't run into any problems at all. It looks like you now have a working version. It sure is nice being able to hotkey my meds, I might even get around to using them now. One thing I did run into when I first tried your mod was that food didn't work right with this eating mod I'm using. I'm using XFO's Immersion Necessities and eating something through a hotkey didn't reduce my hunger at all. I'm not sure if the food healing is working or not though, so that could be just a very minor conflict with some other mod.