Hi Ciao - I think you really should try both a triple and a compact. Is there a shop near you? The compact wouldn't work for me as I miss the high gears. On my triple I rarely use the small ring, but when I hit a big hill I gladly use it. Both my husband and I decided on triples for that reason. Here in the nw, we have hills. My husband can spin a crazy cadence in his smallest gear when climbing and I have yet to see someone pass him going up hill. As for smooth shifting and dropping chains, I have never had a problem. I have ultegra and it shifts like butter even after having well over 2,500 miles on this particular bike and I have never dropped the chain. But...as you have read here, everyone is different in what they prefer and so I wouldn't think of making this kind of decision without testing both.