I ride a Redline 925. I didn't buy it to be hip (my brain isn't capable of thinking in that direction.)
For YEARS I rode a geared bike and always has a 'grass must be greener' mindset when observing SS bicycists. I wanted a ZEN bike to get from point A to point B and back, and not deal with crappy shifts, and the chain locking up or coming off the ring, and obsessively shifting to find the magic place. I also don't have a crapload of time to maintain the geared bike. Sick and tired. SICK AND TIRED. I was sick and tired of geared bikes. Sick AND tired. Both. Not just sick. Not just tired. Sick and tired. Truly sick and tired. Not just overusing the common phrase. I TRULY was sick and tired. If there was a phrasionary (dictionary of phrases) you could look up "sick and tired" and see a picture of me on a sidewalk trying to put my chain back on the ring while making a very ugly face. One might call it the Sick and Tired face.
Guess what? The grass IS greener! S/S works just fine! Sheldon Brown was right! I'm grateful! I'll never go back to a geared bike unless I move to San Fran or want to take up racing! I'm no longer Sick and Tired! I LIKE RIDING MY BIKE NOW! I LOOK FORWARD TO IT! SOMETIMES I SMASH POPSICLES ON MY SWEATY SKULL OUT OF SHEER JOY!!!
Try riding S/S. Just do it. Then decide what you like.