Hey TooManyGuitars.
Let me chime in here with some support. I'm in Melbourne and I bought a Surly Cross Check for AUD1,6000 about 5 years ago (I bargained them down from $AUD1,900). I bought it stock but since then have changed out the saddle (Selle SMP), wheels (Fulcrum Racing 5 CX), Cranks (167.5 Sugino) bought rack (tubus) and fenders (planet Bike). All up the bike probably cost me $2.3k after additions.
What many US MMMers may not appreciate is that Australia has generally higher wagers (for better and for worse) combined with a dollar than only buys US70 cents. So everything here is pretty expensive, and when you import things from the US, they are even more expensive. Also, there's only about 20million people across a continent the size of the US so the cost of transporting things around puts a premium on everything. For American readers, imagine the population of Illinois and Michigan combined and spread out across the entire country. Or perhaps a bit over half the population of California, spread out across 8 states/territories of Australia.
The bike may be made in taiwan but economies of scale and distribution arrangements means that you can't cut out the middle man. I've read posts on Taiwanese cyclist blogs saying that they can't get bikes built in their country as cheaply as importing them!
I think in terms of frugality, the Surly isn't optimal - but if it gives you the same amount of pleasure as mine has it will be a good purchase for you. I do a bit under 10,000kms a year, a combination of commuting, trail riding, road riding and pleasure cycling. The cross check is my goto bike for carrying groceries, picking up hard rubbish, trail riding and last weekend I took it touring for the first time. I also have a Kona Paddywagon single speed and a Cannondale Caad10 but the cross check gets most of the running. When I figured out I could fit a case of beer (24 bottles) in the panniers I finally realised I could sell my car.
Also, buying a second hand bike/ or a cheap MTB and making do, isn't necessarily optimal if you're spending time fixing up a bike when you're prefer to spend that time riding.
I think a frugal option would be to have bought the Cell Brunswick Cyclocross bike, but you can only do that online.
I think a fancier option would be to build up a bike from a Soma frame. Or to buy a Genysis cyclocross bike. Or get some custom Gellie frame. Or Llewellyn. Or BAUM! None of which you have done.
On the East coast you can get a Fuji touring bike or a malvern star for about $1k, but I don't know if they're available to you and they don't really fit in with the same fun factor as the surly. I don't know how many times you'll do it but the Surly's flexibilty mean that you can fit super fat tyres on it and go off trail, or you can run slicks and use it as a road bike (as I did for ages).
But I think the Surly is a great choice in a situation where the options are far more limited than in the US, or even compared to Melbourne.
If you're ever in melbourne and want to go for a ride give us a hoy!!! I'd love to ride over to Perth one day on my bike!