How's the geometry on a Cross Check, it's a cross bike so I'm guessing fairly aggressive? Just wondering if a Brooks is the best choice. I'm sure it's not he most popular opinion, but I found that for anything approaching a racing geometry a standard B17 is not he best fit i.e. if you are sitting forward on the saddle. Plus the added weight, lack of any cushioning in the urban environment, price, break in period and fact it's not waterproof aren't great either. Again, I'm sure I'll get shot down for this, but if you're looking for advice, that's mine!
Plus I would say run to run at least 32mm tires (vittoria randonneur or Panaracer T-Serv's are both great) and get rims that are wide enough for them. You can run wider tires on rims that are not meant for that width sure, but it does make changing the tires a pain.