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All these issues can be addressed during training.
Yes helmet is worth it. So is a decent skinsuit. You can test helmets for aero using rolldown or Chung or paid testing methods but best is to find something that addresses your particular fit issues and try and get the most aero one that fits the bill. I use Bell Javelins - they're comfy enough for 24hr and test fast for me.
TTF has used options you can get cheap to test out.
Got a Garmin or computer? Set an alarm to get you into the habit of eating and drinking regularly. I tended to eat on the hour and half hour and drink on the 15min marks although I'd only bother with the alarm every 30min. It helps me as I would often go hours without eating or drinking and this is sub-optimal when racing.
You need carbs. Find out a way to get the most carbs down and stay down and you're sorted. Fats and proteins aren't necessary until afterwards.
Shoes will need to be sorted. I can't tell you what the issue is but it sounds like you're working on eliminating comfort issues now so that's spot on. Keep doing that. Remember to enter the 24hr too, that helps :)
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hippy
I am comfortable on the bike. I need to change the saddle though. also had a pain in my foot after 10hrs I need to get to the bottom of but that might have been my chilblains which have nearly healed but not completely.
In terms of distance gained how much could a TT helmet provide. The one I have is not that comfortable so I would need to buy a new one. Are we taking a few miles over 24hr if so it will be worth getting one.
I also figure nutrition is critical. There is a club member who has done this several times Dale Sturman but his first few attempts failed due to not keeping his food down.
I have the opposite problem with hydration I often dont drink enough which is fine on a 4 or 5 hr ride to a point but not on a 24hr. A learning curve it will be for sure.