I’ve done the WotR twice and it’s a lovely route (I’ve done the Walney-Whitby and, just last week, the Hadrian’s Wall routes, and it’s the best of those IMO).
First time was with an unfit riding partner, carrying off-the-bike gear staying in BnBs, and the second time was with a group of mixed experience/ability with a support vehicle carrying kit.
Both were done over 3 days, and they all managed the ride fine. I’d’ve loved to do it in two days, it’s very doable. The toughest section for me was from Appletreewick through to Brimham Rocks.
After Ripon it’s nearasdammit flat so you’ll have got the hard work out of the way if you aim for there as your stop after doing Day 1.
One of these[/url] might help with your gear carrying?