How far can you get on one bottle and what constitutes a crazy descent?
Monsal is OK for hill climb but there's not many ways there that don't involve climbing something a bit more serious. And as you'd be right next to it, Sheldon is a more rewarding challenge.
Routes suitable for 1 bottle & 1 brake please, refilling half way... And avoiding crazy descents if possible.
Strava 'min elevation' might help here. Trip to Monsal Head for a little bit of HC?