Interesting question!
Several years back I hunted in Buffalo Co WI. I've never seen so many deer, and big ones too. I shot a really nice buck close to the end of the hunt. It is my biggest deer, but not by much. It is also the deer that I am least proud to have shot. I was still happy at the time, but I knew there were better deer around. I had spent a week hunting already-set stands and decided to hang my own set up where I had seen this deer a couple of times. It worked out, and I was happy to get a shot, but not the same level of excitement I would have felt on my home turf.
I no longer care if I harvest a deer with a gun or a bow. Once upon a time I felt a little better about bow kills, but anymore that feeling has faded. It seems for me if I kill 'em quick and clean, play by the rules, I don't care what tool is used. Having said all that, I don't think it would matter to me if I shot an urban deer or backwoods critter as long as I did it right. After my experience last year, I don't even think the size of the rack matters to me as much as playing by the rules and making it clean.
Everything is a matter of perspective in this thing. Having grown up hunting big woods and hollars, that is what comes to mind when the term "deer season" pops up. I wonder if the kids that grow up hunting urban properties dream of hearing a deer walking over the sound of an Interstate highway in the background...