I did the Wheelright route in three days with a guy off here a few years back, but we did have another guy off here drive a nice big white van for us. (He was supposed to ride too but did his back).
St Bee's --> Ambleside --> Danby Wiske --> Robin Hood's Bay.
1st day was surprisingly easy (and gave us a lot of over-confidence). 2nd day was mechanical after mechanical, followed by bog-trotting for over an hour across ****ing Mosesdale (twice I've been there, twice I've never wanted to see the dismal spot again), and finally being told by our driver at 10 pm just short of Richmond that he was driving us to Danby after getting us a Chinese. 3rd day he dropped us back where we left off, I had a major sense of humour failure with a caravan just before Osmotherly that nearly ended in tears (but did demonstrate I had some energy left after all), then we made it over the North York Moors and nearly stacked it in the dark down the highstreet of RHB.
Would I do it again? YES
Would I want to do it in more than three days? I didn't want to see a bike again for a month afterwards - if I'd had to get on it for another day I may have thrown it under the van.
Will I ever be fit enough to do it again? Doubtful
And great to see you remembered to take pics, Rich, We only managed about three on the entire trip!