I'm also around 165lbs and the steep hills around here keep me in shape. Almost 
all of my miles these days are on a pair of Rohloff bikes and a fixie, but I'm 
in the habit of maintaining and modifying derailer bikes for my wife and a few 
friends, plus I have a few beloved derailer bikes in the collection. Here is my 
current thinking on derailer setups:

110/74 double or triple with bash guard in place of outer ring, 46/30 or 44/28.
8-speed cassette, 12-34

Reasoning: 6/7/8 speed use the same chain. They are cheap, reliable, and 
available with a master link.
8/9/10 use the same hub spacing. So 8-speed is the magic overlap of 
availability, simplicity, and affordability.

Shimano 8-speed bar-end shifters are still available and have a friction 
bailout. I like indexed bar-ends for drop bar bikes where I really want the 
shift to be right the first time. For upright bikes, you can mount the Shimano 
bar-end shifters on Thumbies at great expense, but these days I've been combing 
the local bike collective for 80's friction thumbshifters. I put the classic 
Suntours on my wife's bike plus a friends, and I just picked up the Shimano 
equivalent for another friend's city bike. For an upright bar where the 
shifters are always easily accessible from the grip, I'm fine with friction - 
especially on spouse's and friends' bikes for which I would otherwise be 
responsible for keeping the indexing adjusted!

It looks like 10-speed will be available for a good long time, so you can 
always update the cassette if 8-speed goes the way of the Dodo. AND: weirdly 
enough, Sunrace's 10-speed bar-end shifters have a friction option! (The 
8-speeds don't for some reason.) So 2x10 remains palatable in the future if 
8-speed becomes a parts-hunting endeavor.

All of my favorite crank options (besides Rene Herse) are on Soma's web store 
under Touring Cranks: https://store.somafab.com/touringcranks.html 

If I were buying a crankset new and it had to be square taper, I'd probably go 
with the IRD Defiant and its 94bcd, which might limit you to 30t granny. But 
30-34 is a nice low climbing gear for a road bike! I actually really like 
external BB (Hollowtech) cranksets because they are so easy to remove for 
travel. So if I were building a road bike right now, I'd probably put the IRD 
Lobo on it. 110/74 double, which gives you all the options, and I think it's 
slightly cheaper and slightly better-looking than the Sugino OX cranks.

Finally, 11-tooth cogs are one tooth too small for me. 12-tooth wears out fast 
enough! As goes your cog, so goes your chain, so if you skip the 11-tooth your 
cassette and chain should both last longer - on the order of 10%.

This might not be everybody's cup of tea, but I think you end up with a nice 
wide-range cassette and an all-around ring with a granny bailout, using 
durable, reliable parts that are inexpensive to replace when you wear them out.

Daniel M
Berkeley, CA

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