The latter end of the Ridgeway is a doddle to navigate, just make sure you know how to join up the two ends of trail either side of the M4. Lots of potential to second guess yourself there as the stretch up and out of the village is much further than it looks on a map. Finding your way through the village after you cross a main road about 5m later too I suppose if you've not been there before.
For me night running really brings it all home. You're generally quite worn down by the time it gets dark and can start to experience some pretty surreal moments.
Trust your training too, don't give in to the temptation to push it and do too much this late on. I did exactly this in Jan and am still not back running. I did sneak in the TP100 in May though, mostly walking, no prior training, goes to show how much of it is in the head.
Nathan do a handheld, it's changed a bit since I got mine a few years back (mine is quickdraw elite) but it's probably the best bit of running kit I've ever bought. I tried the Ultimate Direction ones in a shop and they felt fine but the Nathan one easily trumped it. Added bonus is it gives your hand a bit of protection whever you fall over. I can carry that thing for 24 hours and still not really know it's there.
I sometimes attach bottles to the straps of my rucksack and while that's ok, it's much less practical than just having the bottle in your hand ready - I always find I drink less and get dehydrated more quickly. That said, if you can eliminate the bounce then it's workable for races, but in training I'd generally put spare bottles in a pack and stop to refill the handheld. Also... unless it's really hot I'll often be able to survive on the handheld between checkpoints, so no need for the front bottles. That one depends how much water you get through though, I know I drink less than most. If you're in a race and want to use poles then the handheld is not an option, so that's something else to factor in depending on how much spare cash you have and your running goals.
You will get given a bus ticket with a time on when you register to help prevent everybody arriving at the same time. I doubt it matters too much if you're not there at that exact time but it will get busy.
You can always take a portable USB charger and charge up for an hour or so half way through. That said I don't think I'd bother for this race, knowing how far to the top would probably demoralise rather than incentivise! On one climb I remember thinking I must be about to summit for a good hour before I actually made it to the top.
The problem with reps though is you just don't get tired like you do on the long climbs in the Alps. Mentally knowing you've got a 2-3hr constant climb coming is quite draining too where as reps (at least round my way) are no longer than 10 mins max. My best training day for CCC was probably in Brecon, doing as many long topbottom loops as I could.
I think whatever you do so long as you put the time in you'll be fine. Unless you're a keen racer I would try to forget about the clock and just try to enjoy it as much as possible. I started right near the back and a very steady run meant I was overtaking the whole time, nearly 1000 places from first CP to the finish! Having something you can eat at all times will help too. It can get quite hot in the day and quite cold at night so your body can get a bit messed up, I was surviving on noodle soup and oranges mostly, which towards the end wasn't giving enough calories.
The same goes for any night ultra, but if it's cold at night try and be quick through any indoor aid stations (of which there are quite a few on TP). You don't need to stop for long to really feel the cold when you go back out and if you're down to a shuffle then it's hard to get warm again. I was on CP duty at Whitchurch last year and it was carnage with the number of drops. Quite a few left and came back 5 mins later shivering.
Sticking with that, recognise that this is what's happening when you do start shivering after an indoor CP and keep moving, you *will* warm up again within 5 mins if you can keep the effort going. Don't let your brian use the shivering as a way of talking you into dropping!