I live in Shorewood, the first suburb north. Great neighborhoods, fast access to downtown by bike or car, walkable to Sbux or Stone Creek coffee, a couple great bars (one of which is smoke free) and two grocery stores all within walking distance. The lake is 1/2 mile from me, and the highway is close by too. I did most of my training rides from home and went north toward Port Washington. All pretty decent road riding. The swim group in Lake Michigan is great, this summer there was a group going almost every day before or after work, some days both. Lots of great new bars and restaurants in the last five years.
I work in Wauwatosa but wouldn’t want to live there for the reasons above. I would love to have good mtb trails close like Tosa does, and some like the river trail which is nearby, but I’m not a fan. A few of the guys I trained with this summer live southwest (New Berlin) and it seems like a good place to be with kids. If you are looking to hang on to the feeling of Chicago or MPLS the third ward condo developments are pretty cool. For $300k you can be in a sweet new condo near the lake. I like having a yard and for less than that you can get a nice house in the northern burbs.
Tri Wis is a very active organization. Good resource–as an IM newbie this year I took advantage of a couple seminars and a course ride in Madison with the club. Not to mention the discounts at the sponsor shops saved me way more than the membership cost.
This city really is underrated.