I commute on a Cross Check with a rack and panniers and it's great. A plush ride but with a short enough wheel base to be snappy in traffic. I am a big fan of the Cross Check, but it's jack of all trades, master of none. It seems like you missed the bike in Surly's lineup that is most suited for your needs. Did you check out the Long Haul Trucker? Steel frame, upright riding position, eyelets for racks and fenders front and back... Seems like that's just what you need. I'm not saying it's the best choice, but if you're already looking at Surly, the LHT might suit your needs better (in terms of ride position) than the Cross Check or the Pacer.