Katie - sounds like you are working with your vet pretty closely. keep up on his teeth, so that you know that he can chew comfortably. If he still has a problem at all, you can add any of the many cubed or pelleted forage additions which can then be made into a soft mush or even soup. Just feeding a regular feed on the coldest nights and mornings can make a huge difference - fed wet & WARM/HOT. No different then you wrapping around a hot bowl of soup/chili, hot cocoa/cider/coffee/tea, oatmeal or grits on those frosty/wet/miserable mornings and nights.
Something to consider for warmth/support would be leg wraps - either the type you layer on with quilts and wraps (there is a difference to a "stable/standing wrap" and a "working wrap") or just the fuzzy "shipping boots". I had one mare that really appreciated having her legs in her "fuzzy slippers" on the coldest nights and she wouldn't stock up and could still move in the morning. As long as it wasn't raining or snowing, she would also wear them outside in the pasture on cold/windy days - she didn't open the closures, nor kick/stomp them off. You could tell the difference if weather changed and she wasn't wearing them!
and for those of us who have worked in the english horse industry - have you ever used a tool/grooming technique that utilized making a straw or hay "thing"? I can't for the life of me remember what it was called... BUT you make a rope by twisting the hay/straw together, then wind it into a rug/placemat type of "thing". Then, to use it for grooming, you use it like a curry comb in a circular motion to start - lofting the coat. Then you raise your hand/the "thingey" and "lightly & rhythmically strike" the horse with it. It takes some getting used to - for both the human and the horse. This light "striking" and round currying motion causes the haircoat to loft and the blood flow to the skin to increase - creating warmth, too. It's used on the large muscle groups ie: over the neck shoulders and rump. It could be used after work/riding to help with sore muscles, too. Because it also draws natural oils out of the skin into the coat - it developed a beautiful shine, too.
I have used it to help warm/clean up a wet, muddy pony - even in conjunction with blanketing (getting them dry/warm before blanketing). I haven't used this technique on any of our current equine - they'd probably all freak out if I did and I would die of over work myself - but it DID WORK! You do a couple full size horses & you'll build strength/muscle in your arms/chest/upper back w/o ever stepping foot into a gym!! I'm not sure what to Google right now to find this grooming technique and can't remember what level it might have been detailed in in Pony Club. Maybe the folk overseas would know what it's called - pretty sure it might still be used on horses there?
Also, understand on the blanketing issue - you can/maybe should get a layered blanket system. The most used here in NC would probably be a light to medium weight turnout that is water proof. In rain, you would still want to make sure that it's not allowing the horse's neck to get wet and that it's not leaking over the back/loins/rump - you can get different types of water proofing "stuff" to redo your blankets. They usually have to be re-done anytime you wash them. You could layer it lighter/heavier liners (they have both slick and fleece) or actual blankets with fiberfill. When I worked for a boarding barn, we had 12 that were blanketed for different reasons. Several were due to age/lack of coat - all were "work" to keep up with based on weather. BUT they were comfortable, LOL. Each owner provided 2-4 blankets that could be interchanged/layered. And in the worst weather, the stalled horses weren't turned out OR they might get turned out 1/2 way thru the day. More than once, when horses were left out at night and the weather changed I was out between midnight and 3 am, pulling wet and/or blanketed horses back in. Thru-out the day, I would check blanketed horses - horses who were wet under blankets either due to sweat (too hot) or due to not having enough protection from driving rain - got blankies changed out. Owners were kept informed if they weren't coming to the barn regularly. We didn't provide cleaning or repair services, so owners had to take care of that. Really soiled blankets lose their ability to work well, too. Some horses naturally seem to get theirs more dirty than others - even in the same pastures. It is amazing!
AngC - if the horses are "crapping" on their blankets - their owners aren't caring for them. The blankets are either too big or too small (gaining/losing weight can change the size of blankets). These days, most are made so that the tail is either not covered at all or have a proper tail gusset that allows the tail to lift and won't soil the blankets or the straps utilized to keep them in place. That said, there are also horses out there that can still soil them and seems some just delight in doing so! But if the blanket is heavily soiled - again - the owners aren't checking them enough.
I hate driving down the road and seeing horses blanketed when the temps have shot up over 60* f. Most don't need to be blanketed and will sweat (a lot) at those temps when they are. If the blankets are left on, then wet, the horse's health can be compromised. Again it's usually because an owner has left for work/school and didn't remove the blanket(s) before leaving (or an employee is working on a different section of the farm OR "slacking"). I've often switched out with some friends - when I was working later I would swing by their place(s) and remove blankets/check horses and when I've had to work - I've had others do the same for me. One of the reasons I do hate blanketing these days is because the weather has been so "wild" and it's "work" to keep up with it - in both directions.