Kenmore Square, Boston to Norwood over 30 years
Route: Reverse commute from downtown on four different routes of a minimal distance of 14 miles, each defined by a different hill; can expand to about 30 miles to train
Environment: In order of hill difficulty: Gritty urban, pleasant suburban, pleasant urban, ritzy suburban
Hills: One moderate hill on each route, then smaller hills; estimate only about 1-2 miles flat
Frequency: Variable over the decades; currently about 50% in winter; 75% nice weather (work is an obstacle)
Bike: Specialized S-WORKS CF Road Bike; Cannondale beater mountain bike (fenders and Marathon Winter studded tires)
Bike name: NA
Cargo: Ortlieb panniers on the Cannondale; backpack on the S-WORKS
Helmet / Mirror: yes and yes (left and right Take-a-Look eyeglass mounted mirrors)
Destination:
Parking: inside about 100 feet from my desk, directly through a door from the outside
Cleanup: shower facilities; place to hang clothes, and a table fan available to dry; for most of the time I wear surgical scrubs
Amenities: coffee shop and cafeteria on site; almost all my personal service needs like barbershop, dentist, dry-cleaner/tailor, supermarket and drugstore, and good take-out restaurants are all within walking distance of work, or a short hop on the bike; bike shop two blocks away
Alternative Transportation: train, car, bus, taxis, car rentals, Zipcar, place to stay comfortably overnight.
If anybody is interested to describe your commute, here's the template...