I’d consider joining the Youth Hostel Association, this will cost you a fraction of the others, but you will have to do much more research for yourself and be more self reliant. How could you resist the chance to stay at the Hostel at Boggle Hole ?
You’ll have to book each place yourself, but its easy enough.
Most of the routes that do this completely miss out Rosedale, which is something of a shame.
The old railway that used to encircle Rosedale Valley and come out the top of Ingleby has made for a very good cycle and walking route.
You see that picture of the Ingelby incline in that link, at the top there was a winding engine that pulled up the ore trucks, however, for the train engines that transported the ore around the valley, these also had to be pulled up and over the same incline. The only way it could be done was to take out the large driving wheels and so reduce the number of axles to two, instead of four, which would have made them seesaw dangerously and get outof control - once these train engines were in the valley, they stayed there until they were broken up.
I can understand this as this valley is almost at right angles to your route, but you do actually skirt the northern edges of it.
There are some wallking routes that take you from Lastingham down to Rosedale Abbey, where you could have a walk up the infamous ‘Rosedale Chimney bank’ -which is so steep that while you walk down it, your feet slide forward in the shoes and squash your toes!
If you do go up there, you might wonder what its like to cycle up it, it is interesting, your front wheel often lifts away from the ground and you end up part wheelying.
I highly recommend that you are well prepared for wet weather in the first half of the route, the second tends to be drier.
I would suggest at some point you have a days run, go as far as Grosmont and do a days worth of double back on the train as far as Castleton.
I know the area well, its an extremely good mountain bike route, the traffic is light, but you need to either be extremely fit and have ultra low gears, or have comfortable walking shoes.