I have done this twice.
Once, in 2003, in December, and again in 2004 as part of a longer trip. The December trip was over 3 days. Day 1 was Whitehaven => Penrith, where I stayed in a B&B. Day 2 was Penrith => Allenheads, where I stayed at the inn. I had originally planned to stay at Nenthead, but everything was shut as it was December, so I called ahead to Allenheads and the inn had a room.
That was definitely a good place to stay. As for it being ‘creaky’… Well, I was lying on the bed thinking about going to dinner when there was a loud crash outside the room. Having been told there were builders there I thought nothing of it, but it transpired that the ceiling immediately outside the room had collapsed due to a leaking roof. Then I lay on my bed looking at the cracks in the ceiling above me.
The food was great. The final day, the weather actually turned nice and I had a lovely final day into Newcastle. When you get to the start of the Waskerley way, there is a cafe. When I did it, it was still being renovated and the cafe was a caravan outside the house. 3 bikes were sat outside so I went in and had soup and a roll, apple pie and custard, and a cup of coffee for the sum of £3.50. The other cyclists were firemen from Stanley out on a day ride.
Once I got to Tynemouth I cycled back to Newcastle for a hotel. There was far too much food there.
The 2004 trip was 8 days doing a loop from Newcastle to the Borders, Carlisle and then the C2C route. I took 5 days over it that time but despite the extra load of camping (about 25kg of luggage) I got up all the hills. The climbs that stick in my mind as tough were the one out of Garrigill and the climb out of Stanhope. I visited the same cafe, which is now a proper cafe, hopefully still going.
The 5 days on that were Workington -> Keswick via Whitehaven (iirc - I think I camped outside Workington for £2.50), Keswick -> Campsite on the A66 near Penrith, then on to Nenthead where I stayed in the bunkhouse, then on to a campsite near Consett, then final day Consett->Newcastle where I stopped and caught the train back south.