Commuting - Upgrade CC, Buy New CC, or Buy LHT?

So, I got into riding about 18 months ago. I was up camping along the
NorCal Coast and through Oregon. I saw these fools riding bikes loaded
down and wondered what they were doing. I spoke with some and found
out about touring and thought it was the coolest thing as somebody who
likes to camp/hike/etc. When I got back I started reading some blogs
and Crazy Guy on a Bike and decided to pick up a bike. I bought a
cheap RockHopper on CL, not knowing if it would stick, so wanted a
bike on the cheap.

At first I could ride a mile or two and it was most around crowded
SoCal streets, so I don't like it. Then I moved one block from the
beach and the nice bike trai. So much better riding and it started to
stick. So, knowing touring might be a long term goal and that I'd like
to maybe commute and get into longer rides (no roadie racing or
anything) just cruising, I decided to get a Surly. I like the bigger
wheels of the CC for my size (5'6-5'7), so opted for it over the LHT.
I hated the '09 CC colors, but luckily found an '08 in mist grey on CL
in my size. I still don't know much about bikes, but at $850 was in
really good shape. The thing that I didn't realize is that the
drivetrain isn't for me. The guy built up the frame and it has Dura
Ace crank (59/30), DA de-railers, and a 11-25 cassette. I need more
relaxed gearing for cruising and climbs.

I asked on-line and went to a couple LBS and they said because it was
more of race/roadie components I couldn't just swap out one piece
because things were not compatible with the larger de-railers and
cassettes. The cost to swap out the drive train to something more my
laid back style was $$$$.

So, long story short I was thinking maybe I was just better off trying
to sell on CL and buying one new that better fits my type of riding.
It seems that may be cheaper. However, I am not too fond of the
current CC colors. I really like the grey. I also like the new LHT
blue. I do like the 700cc wheels though. I started getting MTB this
past fall and picked up a steel 29er Salsa El Mariachi. So
even my MTB has the big wheels. It is only 1x9, so I have to do a lot of hike a bike at this point.

I also saw that REI as 20% of the Randonee and I have a dividend, but
the gearing doesn't seem optimal either. I really am thinking some
touring at some point. As a teacher I have the time to do it. In the
mean time I commute to work (~3-5 miles), I do 30 mile rides on the
weekend (slow getting into shape and eventually want to do longer),
ride to get stuff to eat, etc. I have Ortlieb panniers so I can take
my laptop to work, bring clothes, books, food, etc. I even do short
grocery runs.

59/30 is an odd sized crankset. You think maybe it's 50/34 or 52/39? You could probably get away with a 13-34 new rear casette and a long cage XT rear derailleur. Add new chain and cable that'd run you around $150 if you can find some deals and DIY.

About three years ago I was in pretty much the same position as you. I wanted a touring frame with 700c wheels. I asked on the touring forum and pretty much got talked into the benefits of 26" wheels. The LHT is a really nice relaxed ride with low enough gearing made even slightly lower by the 26" wheels. All things remaining equal, a 26" wheel is stronger, and the wheels that came with my LHT have remained true for over 2000 miles now. I would ask for more opinions on the touring forum, not to say there aren't really smart people here, but the touring forum might include a few people who really get into the nuts and bolts of touring frames.

Typo. lol 52/39.

If the components are in good shape and of recent vintage, you could almost certainly sell the dura-ace components for more than enough to cover a conversion to a Tiagra/Deore mix with a triple crankset and MTB cassette. The Dura-Ace components should all have a number stamped on them somewhere. If it's 7800 you're good. Lower than that may still work. People love the Dura-Ace parts.

You could also save a bundle by doing the work yourself. It's really not that hard, and the knowledge you'd gain by doing it is well worth having. The LBS can back you up when you mess something up, or if there's a bike co-op around you they might even help you as you're learning. Check out Jenson USA, Blue Sky Cycling, Price Point, Nashbar and Bike Island for parts. Ask here if you need help figuring out which things go together.

Cruise on over to the touring forum... I think those guys can give you excellent advice. I think the crosscheck is a great frame. I think it would do fine for light/medium touring duty. Having a double chainring/crank isn't the most ideal setup for touring but it could work. Most definately change out the rear cassette to something like an 11-34 and you'll have to go with a long cage rear derailluer.

Like a previous poster said, I think you can expect to get some pretty decent coin for those dura-ace parts.

Like a previous poster said, I think you can expect to get some pretty decent coin for those dura-ace parts.

I think they are a couple of generations old, but still quality components. I posted on the touring forum, too. I'll see what comes up.