On paper I'm sure this is a simple answer but I'd like opinions on my personal situation.
I grew up on BMX bikes and in my teens I got a Cannondale mountain bike.I stopped riding for most of my 20's and in my 30's I bought my first road bike, a cheap Takara Kabuto single speed. I've had it for 2 years and just started riding every day for as my main transportation about 3 months ago. I have replaced bars, brakes and tires but now I think the cheapness of the materials is starting show after riding it more frequently. I have also realized that the bike is a little too big for me (it's a 57 and I'm 5'10" and inseem about 33).

So now I want to get a good all around bike for commuting, errands, fun, exercise etc. My main wishlist was ability to fit wide tires, braze ons for rear rack and bottle cages, brakes and drop bars and I was leaning toward gears to help with hills, wind and when I'm hauling stuff on the back. The Cross Check seems perfect but a little more then I wanted to spend and then it went on sale for $975 at REI and I decided for that price I should just get it. But now I'm starting to have second thoughts about the gears. I had the one mountain bike with gears and to be honest I hated gears and never know what gears to be in (a little education can fix that I'm sure). But I am just getting to the point on the single speed where hills don't intimate me and I'm starting to really appreciate the simplicity of not having gears to think about. Of course I can get the Surly, ride it for a while and then covert to single speed. Then I started looking at the Kilo WT and it seems to have everything I want except gears (which I am not sure I want) and a decent frame for half the cost.

Is the Surly bike minus the gears worth $500 more then the Kilo WT? Also factoring that there will be cost in converting to single speed and I would probably have to pay a shop to do that for me. I have the money for the Surly but it's more than I really want to spend on a bike right now. I don't have to put it on a credit card or go into debt but $500 is still a chunk of change to me. But if it's that much of a better frame and components and it is going to last much longer then I would certainly spend the money now. My only other concern is locking up around L.A. although most of my riding is in nicer areas with lots of police patrol.

I ride a Cross Check with gears and I love it! It has been my primary commuter vehicle for approximately the last 5 years. I've never ridden the Kilo so I can't really compare the two. I would say, though, that if you want a single speed Cross Check it would make more sense to buy it as a frame set and build it up that way rather than buying the complete (geared) kit and stripping off the derailleurs and converting it to singlespeed.

Thanks. I have never heard anyone that owns a Surly say anything bad about it so that is another reason for me wanting to get one

Cross Check gives you way more options. You could build it up SS now and add gears later if you like. The WT doesn't offer such a luxury.

For comparison purposes with the Crosscheck, it may help to know that the Kilo WT frame is a knockoff of the Surly Steamroller.

^ yes.

The Cross Check is not really a comparable bike to the Kilo WT, as it's a geared Cylocross bike. If you really want a one-gear Surly, you should just get a Surly Steamroller. It's cheaper than the Cross Check, and it's already a single speed, so no need for a conversion. The Kilo WT, from everything I understand, is basically the same bike as the Steamroller, but at a fraction of the cost. The Steamroller doesn't come with drop bars, but if you buy from a shop they may switch the bars for you at no cost. That's what a friend of mine did.

I know it's not a true direct comparison. The Steamroller doesn't have rack braze ons so if I go single speed I figure the WT has everything I want out of the box.
If I wanted to convert the CC in the future would it be as simple as removing derailleur and cassette and installing a new cog and chain or would I have to replace the rear wheel or crank?

Yes.

Seems like it'd be easier to remove the gears from the cross check than it would be to add the them to the kilo wt. On the other hand, if you're sure you'd not need them ever...

Do you live in an area with an active craigslist? Maybe you could get the Kilo WT and find a pretty decent used geared bike for the cost of a new Cross Check.

You could always use P-Clamps in place of braze-on's.

The kilo's rear stays are 120mm. Unless you go IGH you won't be able to go to gears on it. The Crosscheck is super versatile. There is also a single speed version available now. No need to convert.

https://surlybikes.com/bikes/cross_check_ss

Thanks. I have seen the CC SS but price is about the same as the REI sale price for the regular CC. I hate flat bar so I figure if I bought the CC SS and then had to swap the bars and brakes to drops that is going to cost more then buying the CC on sale from REI. I think I'm going with the CC and try riding with gears for a while. If I find it beneficial for my commuting and utility stuff then I'll probably just buy a regular Kilo TT later on for a round town ss/fix. If I don't like the gears, I'll convert the Surly. I will also still have my current single speed although I commuted today and it sounds like the cranks are about to pop off and the bb is going to spill out on the road every time I pedal.

good move. if i had the funds at the time, i would have gotten a cross check myself