Now, I'm going to say this once, and once only: although a new outlands map would be nice, we can't have a "town" like you suggested. It just wouldn't fit canon if the Combine left a town in the outlands unscaved, and before you say we rebuild a town the Combine would just come in APC's and roll over the entire thing. If we were to have some kind of town, it'd have to be hidden, the only thing I can think of is underground, or in the sewers maybe. But, on the map change thing, on the fence about it. Because I actually kind of like outer canals. Its not too buggy, it doesn't attract many minges, and its well made.
Thats just my two cents though.