So to bring this back....I picked up a compact 50/34, and have ridden (futile attempts) with a 53/39 and an 11-21 In the rear
drooling
which was fine on the flats, but I did note that I was typically in the middle range (~14/15?) 27*53/14 ~ 102.2 gi vs a compact 50 at say 12T in the rear which gives me 27*50/13 ~ 103.8 gi so my riding in the flats won't change so long as I go with a 12-something cassette, longer hills were an almost always painful task in 39/21 ~ 50.1 gi so (and here comes what I was debating) if I stick with a 36T on the inside to preserve shifting goodness ...assuming this is needed... with an 11-23 I get ~42.3 gi which is akin to a 39/25 combo...which should be okay. If I run a 34T inner chainring that drops to around 36.7 which akin to a littler lower than running 39/28 which seems like a serious climbing gear, but with the same spread in the back. That makes me a little nervous since I might end up having to flip flop between big rings too much :/
So then the big finale question is whether I should get a 36T chainring and two cassettes one for flatter rides and one for steeper rides or should I leave the 34 on and just get 1 cassette that'll cover most of my bases. I like the ease of the latter, but the shifting issues I've been reading about seem annoying. Realistically though a 36T ring and an 11-23 should be good for most everything I ride regularly though, just without a few of those extra lower gears.....maybe my fitness will make up for them eventually
These may all be just personal problems since no one can really gauge what's good for you without being you, but I feel as if I ironed out some of the confusion by just writing it out.