What do you want out of this city that is bike related?
A wide selection and/or variety of road rides? Solo or group?
A community that you can cycle around for your day to day activities?
A community that shares your (non-cycling) interests and has hard connections to support them?
My general observations are that you can find a bike friendly community/location within so called bike unfriendly cities and find bike unfriendly community/locations within so labeled bike friendly cities.
Al