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I definitely use a combination of elevation and distance to plan routes. I also know that the steeper the grade (for the same rise), takes more out of me.

Over my short biking life (3 years), I've averages 89.9 feet per climb. I've been on and due to injury so I've probably never gotten my legs as strong as they can be. But I always wonder why people say biking is an aerobic sport. Give me 30 miles and 3000 feet of climbing and my legs feel a lot like I just did squats. Note: I am a fat ass @ 5'10" 195lbs.
 
100'/mile is less than a 2.0% gradient. If that's a "hard ride" around your area, you've got it really easy. I live in a neighborhood where the hilly roads are more like 6% gradient.
We're talking about the entire ride, not just the climbs. You still need to ride to the climbs, and ride back home; the actual climbs will need to be significantly steeper than 2% in order to hit the 100'/mile. Here's the elevation profile for that 100'/mile century I was referring to earlier as an example.
 

Don't mind the music.
Lol the wind in that video looks absolutely demoralizing! The worse wind I ever encountered was on a local Tuesday night hammerfest where it was basically a race with no prize but glory. All race tactics applied and this was not only a drop ride, but a try-to-drop-as-many-as-possible ride. By the time we got to the long 5-mile straight and flat section, the wind had shifted and was a direct headwind. I don't know how fast the wind was, but our usual clip of 30 mph or so (at a firm but sustainable pace) was blown down to 12 mph at close to max effort. You know it's sad when you see a paceline of half a dozen guys absolutely drilling it and only going 12 mph.
 
I too live in the Bay Area, Ca. I have been riding for 30 years. Just came back from a long layoff due to an injury. I have really enjoyed the Garmin. I started riding again in May at about 240 lbs. I'm 6 foot four. I'm addicted to climbing more than I ever have been. I wish I had longer sustained climbs. Without traveling a bit. Just did a 75 mile ride with 4500 feet of climbing. I'm really enjoying being back on the bike.
 
Many things can influence effort, hills, head wind, tail wind, road surface condition. I pace myself, I ride close to maximum effort. Time on the same route can very depending on wind. I'm very aware of how many miles I ride, but I look at my time to estimate my effort. I love hills and look for them, sometimes doing intervals on them, I find that time gives me the best indication of how hard I rode, because I know my effort is pretty consistent.
 
I normally focus on time, not distance or elevation really - then for a given time it depends on what my purpose for the day is - if it's training then I'm doing a targeted power output some how either intervals or NP over the ride or average power etc. If it's a fun ride with a group, it's normally planning how and where to either inflict pain on others on a long pull and/or win a few targeted city limit sign sprints etc.
 
Got a link to that hard route? I might give it a go when I am out that way
Pikes Peak from the west side of Colorado Springs. You can also make it shorter starting from Manitou or from the toll gate. Ripping good descent.
 
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