This is my first 1000 so a little nervous. How does one plan and work out time stops once we go to to multiple days?
Your build up looks just fine and very sensible.
As far as I see it, and I haven't looked in any great depth, we stop at fairly sensible distances at Hawes.
From the website, day 1 is 270km (we don't start until 10am) - hard terrain, but that's going to be 15 hours for an average rider I am guessing - so back in for 1am ish
Day 2 - 355km - the terrain looks on paper to be slightly easier than day 1 and 3 (famous last words!) - even in easier terrain, this will be a long day, so I'd guess people would want to be on the road at 5-6am to be back midnight-2am that evening.
Day 3 - 280km - hard day by the looks of it! Try for another early start and try and be back for midnightish.
Day 4 - 115km run in to the finish to be there by 1pm, so as long as you're on the road by 6am you should have a good chance of getting the job done.
Looks a well paced ride to be fair. It's not a race, so make the most of the structure and try and get a decent bit of kip each night before heading out early to get the next day done. That's the plan I have anyway. Sounds easy! I am sure it won't be, but if you start falling behind on sleep from night 1, then things get progressively slower and harder!