Hi,
I started the Way of the Roses just a day or two after your posting. I did it in four days. I arrived in Morecambe by train @ 1239 and started from the sea front @ 1300. My first night was at Dalesbridge in Austwick, the second in Pately Bridge, the third night near York, ie at home, the fourth I spent night in Bridlington. On reflection I could have made it home to York, by train, on the last day as I arrived in Bridlington at 1520 having done 60 miles, partly due to the prevailing wind.
For once I was fortunate with the prevailing wind. I did the ride on a mountain bike with off road tyres and I was clocking 18-22 mph from near Ripon to Boroughbridge.
Where do I start with your questions? The first day was not too hilly but it did give a hint of what was to come on day two. Day two, Settle to Airton - WOW! Clocked just over 40 mph on the way down into Pately Bridge later on, with the brakes on! - make sure your brakes are in working order and don't "drift" around the bends. Exhilerating. Day three, After Brimham Rocks the route levels out and is relatively flat across the Vale of York. Day four is the flattest part of the trip so I made it the longest in distance of all the days.
There are cafes, tea-rooms & pubs all over the place but it will depend on your timing as to whether they are open when you arrive. I missed out on a main meal at the Croft Cottage, Austwick because I arrived too late in the afternoon, but there was the hotel.
I could rattle on forever.
You'll have a great trip.