Out of curiosity, where are you finding 20% grade paved roads that last for a mile? They don't build mountain roads like that where I live, just urban cross-streets.

my C'dale r2000 came with a 12-23. I recently chaned ir out for a 12-28... Big, big, big difference. I ride on the weekend with a guy that is 20 yrs younger. I used to get to the top of hills not to far ahead of him on the 12-23. Now I end up waiting up for him at some point on most hills with the 12-28.

Go for the 12-28. You won't loose much on the speed end but the gains going up hill will be worth the spread of gears. Now, I go looking for hills and I'm 51.

I'm 17. I weigh 140 pounds. I have a 12-27 and a 39-53, and I still suck at hills.

I think some of it is genetic, or just practice. I'm a decent sprinter.

keep riding. when i was younger i used to do hill repeats and it payed off.

I'm 53 years old, 210 lbs and ride between 17.5 & 19 mph average on flat 30 to 60 mile long rides.

I use a standard crank with an 11-23 and like it. However, my hills are less than 10% here in Illinois and less than a mile in duration.

I also ride some steeper hills in Wisconsin, these are more than 10% for a mile or two with 15 to 22% sections. some days provide more than 10,000 ft of climbing. I use a 11-32 with a compact crank.

I would consider a 12-27 cassette. It's an easy change and should provide desired results.

When riding for fun, I used to love my 50-34 crankset. I still think a 50/36 is the best all around crankset for new riders and even some experienced ones. Just keep 2 cassettes handy. A 12-23 and a 12-27.

As for the OP. I think a 12-23 and a standard double sounds painful. I like to ride easy every now and then and the 39-23 sucks if you want to just go out for an easy ride. Egad, sounds painful!

a 1000+ft climb must be pretty rare in wisconsin.