I think you'd get more benefit from an extra rest day midweek and would sack off the Weds runs. Move that mileage to Sunday which generally looks a bit short imo.
Dont think it's sensible to pencil in runs so soon after RW and W100, it's just asking to get injured, and if you skip them then mentally you'll be behind schedule. I'd leave those weeks clear until the Sat and if you feel like a gentle pootle towards the latter part of the week then treat is as a bonus.
Schedule seems quite race dense too, Ladyblower straight into Loch Ness means the first part of your 2 week taper for W100 may in effect be recovery instead. Maybe drop a run in your taper weeks too, you'll not get any benefit from 888 vs 8R8 so I'd take the rest instead.
I'm not the most experienced by a longshot but I've done a few 20+ hour efforts now. In pretty much all races, certainly the longer ones, there have been periods of genuine misery, not necessarily in the latter parts of the run either. It's at these points your brian will try to get you to stop, dreaming up excuse after excuse to give you a reason to back out - this hurts, it's pointless, I've done enough to be happy etc. I think this is where really wanting the finish comes in, it helps you disregard the thoughts and keep on moving.
As Kevin said, music can be a real help. I never listen to tunes when training either but always take them with me on long ultras, it can be such a lift especially when spirits are starting to wane after a long day. It brings some familiarity and helps take your mind off what you're doing.
57m is a decent effort and you should take a lot from it. It sounds like it was your first experience of dealing with nutrition, darkness, cold etc on a long run so you'll learn loads from it to better prepare you in future. Until you've been through it it's easy to think "ah yes, I like jelly babies and fig rolls and sausage rolls so they'll keep me going" without realising how unappealing these things may seem 12 hours in. For me, forcing yourself to eat when you feel sick is one of the hardest parts, but it's vital to keep the calories going in otherwise the downward spiral will only worsen. I find bananas and oranges are a life saver, they always seem to go down ok and often make other things more enticing. Coke is also a winner if they have it, for a while I turned my nose up at it but it always seem to go down well.
Don't give up on the ridgeway just yet, it's just planting the seeds for another DNF. Spend the next 2 months visualising it:
- putting yourself in the position of hitting 60 miles with a 30 min cusion on the cut off
- picturing the sun come up and turning your head torch off
- finally turning off the ridgeway and hobbling into avebury.
This will help prepare you for the day and when your brain starts pestering you to stop you can tell it to shut up because you want to experience those things you've been visualising for real.
It's also really important not to get hung up on things that don't go to plan. If you make a navigational blunder and do an extra mile, fall over and hurt something etc it could weigh on your mind and be the root cause of a DNF. Tell yourself to forget about it, it's done so move on, then your brain will have one less argument for quitting when things get tough. Recognise that there will be peaks and troughs, if things are sucky then just tell yourself it's normal and that in 10 mins you'll feel a bit better. If you get bogged down with negative thoughts while going through a trough then your giving your brain all the ammo it needs to get you to quit.
I've got the goretex version of these for my daily walking about shoe and I think they are great. There isn't much cushioning in them and they generally feel a bit minimal but are really comfy and I would imagine great for running in. As a crossover trail/road shoe I'm not convinced though, maybe ok for very light trail but in those circumstances road shoes are probably just as good.
For gaiters, the ultramarathon running store sell dirty girl gaiters in a load of different patterns. They don't stop the very fine stuff getting in as running shoes are generally quite holey, but they do reduce it significantly and obviously stop stones and the like finding their way in.
Congrats on the finish WR. I pondered if I'd run it again too and am currently in the no camp. I think I'd get more from taking a training week there and hitting the trails at leisure without all the crowds. I'm not sure what time you'd need to aim for to lose the in-race crowding, but I reckon it would be pretty sharp. Dunno where you finished but I was 14:08 and was bumping into lines all the way to the beach - I reckon 60-90 mins quicker would have been just as busy as that would be peak marathon time and I can't see me ever getting much quicker than that.
I think mid-packers in these big field international races have to accept it's a nice day out and forget about position and time as much as possible.