1) Yes, Your assumption is correct. Ride from the door, plenty of challenging uphills, great downhills off the commons and through woods.
Plenty of areas to link together towards Cranham, Painswick, Nailsworth, Dursley.
2) I’d love to know? Most of my cycling is by myself. Interested in the replies to this. I did one ride with the Cotswold Massiv, figured they had become even more niche! Where do we find information?
3) There are some excellent pubs selling beer from local breweries in Uley, Stroud and Nailsworth. Finding a good pub will not be an issue.
Re: House Hunting.
Check the aspect of any house, sunny side of the hill at different times of the day. Some of the valley bottoms are dark and cold, get a sunny spot on the hillside and you have epic views and evening sun.
Parking can be a major issue, offroad parking may be important. If you want an example of this drive through Chalford or Woodchester on your house hunting trips. Narrow roads, cars everywhere.