I guess the million dollar question is what you want it for? I love my Surly to pieces (also a crosscheck) almost literally but unless you are into actual cyclocross you have to remember that it is a bit of a compromise bike. Jack of all trades master of none which is why I love it. It is slower than a road bike but faster than a commuter/mountain/hybrid whatever. It is not as sturdy as a mountain bike but sturdier than a road bike by miles. It is not as comfortable as a cruiser/hybrid but much more forgiving geometry than your average road bike.

It is perfect for me, it handles long rides well as a result of its more relaxed geometry and is light enough and has tall enough tires that I'm not struggling to keep up with any but the most dedicated roadies on a casual ride. It is a terrific commuter bike because the absorbent steel frame and the fatty tires can cope with all the potholes/streetcar tracks/curbs and idiot drivers that get thrown at me but it is still fast enough to make great time. It can obviously manage some flat dirt trails as well. I even use it for the short triathlons I do because I know full well that I don't train enough to be competitive such that a time trial or advanced road bike would make a big enough difference in my time.

You would not, however, use this bike if you wanted to get into serious road racing or any real mountain biking. You would use it for commuting, casual road rides, light gravel/unpaved roads etc. Oh...and winter...it's a good all season kind of bike. If you get one make sure you get fenders (Surlys like to get wet - steel frames notwithstanding) and think about getting interceptor brakes if you are going to be doing a lot of commuting (lots of stops).

Happy bike shopping.

Mel