I feel moderately qualified to respond to your question, having just gone through the whole thing myself-- converted to a single speed, found it wasn't for me, and got a new geared bike and sold off all the ss parts.
I found that I really liked the single speed (which may not have been the case with fixed gear) EXCEPT for the one hill that I needed to climb to get to my house. I found myself making excuses for why I shouldn't ride that day and took the bus instead.. I would even ride to work/school and then take the bus home (our buses have bike racks) to avoid the hill.
If you're at all unsure of your abilities, I would definitely recommend getting a flip flop hub and doing ss before going straight to fixie.
You would definitely be a stronger rider... and as far as getting in over your head.. I don't think so. There are so many resources and websites you can consult, and if something is too hard, just go to your LBS to ask for help. Don't be scared off by the project aspect of it. On the flip side, do your homework and get advice on your particular bike and your riding needs/wants before doing anything major.
Deb's advice is good. Beyond that, maybe even try to borrow someone's ss or fixie for a test ride. Now that some of the major companies are selling ss/fixie bikes, you should be able to try one without too much trouble. I was definitely walking up the hill to my house, but I didn't feel like a poseur. You should think of it as just different. So many people ride them now (at least where I live) that it's really not a club anymore.. Good luck in your decision! And don't worry too much.. if it doesn't work out, just switch it back and sell what you bought.



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