"Sprain my ankle and yet have to walk out", it's rare that with a sprain you can't walk/hobble to some degree. May take a bit longer, be sore, but if required you could strap ankle with a bandage, or some Duct Tape to keep it stable. Oh and keep boot/shoe on, or foot will swell up and you wont get back on again.
The only time I'd think of using a pole would be for a broken leg. Even then if you don't have one could find a straightish bit of wood, or the like. You can even use other leg as a splint, bandaged/taped together. But that means you can't walk at all and you will need carried off, weather by party your with or MTR.
Unless I was leading a group of more than 3, I woudn't carry a large FAK, plus any painkillers I'd take would be for my use only. Under the lateist rules you are NOT permitted to give any painkillers to others. You can give them most of their own medication, like Inhalers, but only if they have with them.
Even if they have have painkillers with them, YOU can't give to them. It's up to them to decide to take them, so is not your responsabilty.
I'd echo the recommendation to change your baselayer material. Most of the stuff you take that I don't can probably be explained by the following phrase:
In the medical kit, carry anti-diarrhea meds, I carry loperamide (brand name: Imodium) - I have needed that once when I didn't carry it and don't want that to happen again
With the exception of that type of "incident", a proper baselayer will mean that dry underwear is unlikely to be needed on a day walk. Same with the toilet roll.
Kind of to echo Husky...your first responsibility is to yourself and no-one else.
If I am out solo or with a mate, I carry a small FAK along with a small kit selection of stuff like cord, heavy duty velcro straps for the occaisional...ooo...that shouldnt have broken moment. I can help other people with that kit - I do not set out to do so and if asked assess what I am being asked to do (99% of the time I just point downhill).
If I am out with a party I carry a full leader kit and, unless the situation is life threatening, always decline to help. My responsibility is to my party, no one elses (that said, I have intervened on more than one occaision where the other party were about to call out the MRT or were in some difficulty)
My summer pack - its a 30l but never full, my winter a 55 l - the 30 l is just too small extra insulation, 55L way too big, thanks for compression straps.
It also depends on what way you 'run', some, like myself, can get away with higher rated gear than others, IE. I can use a +5c sleeping bag and be warm at @ -4/5c inside a tent. Other peeps may need to use minus say -10c in the same conditions.
The last meet I was at in Ireland, Wicklow, temp. got down to @ -2c, I'd a +5c sleeping bag and had to take some layers off as I was to warm.
All my kit for the weekend fitted into a 35l 'sack, but that is only because I don't have to carry bag, jackets, etc. for temps. as low as some peeps. Therefore I can carry lighter, smaller kit.
As I said, some peeps can take cold temps. better than others. It's they way we are.
I've bivvied at @ 3700m in winter, @ -35c, with a -25c bag, high rated down jacket & trews. Pal with me had same gear but a lower rated bag @ -40c. I was warm as toast, he just about kept warm.
Oh was an outside bivvy, not in tent, tarp or snow hole, lying on ledge, clipped to 'pro, so didn't fall off.