1) Depends on the walker, really. You are more likely to get disapproval from the farm you have to pass through at the bottom on the other side.
2) From that direction, bit of pushing on the way up, fairly well-maintained singletrack with some steps on the way down. I’ve only done it once, from the other direction, which was more rideable, I’d say.
You could drop into Littondale via Dawson Close instead, then back up at Arncliffe Cote to Malham Tarn, which I would only recommend in the current dry conditions. The PBW section over towards Langcliffe is a fast bit of track, I’d recommend not bothering to drop to Settle, but keep following the PBW rightwards, down to Stainforth, then minor roads up to Wharfe, BW to Thieves Moss and Borrins, then either turn R and head into Horton, or carry on up to Old Ing, pick up the Pennine Way again and follow that back into the village.