Hi Vic
The cities you mentioned are all nice in their own ways. Rhinelander & Hayward would offer more of the "northwoods" feel and have a bit more to offer in fishing. Many many lakes nearby to pick from. Eau Claire & Chip Falls areas are a tad more urban, although not too far of a drive to get away and find seclusion. If the shopping and city life is what the Mrs wants, perhaps those cities would be the perfect compromise. However, all the cities you listed have wal-marts, among other chains, if that helps as a gauge. You mentioned hills for the wintertime. Wausau might be the best bet for that. Skiing at Rib mountain is popular. The other areas are relatively flat. I dont think you can go wrong with whatever of the cities listed. They are all in the northern part of the state. The best region of Wisconsin for outdoor activities.
As for bears - No doubt the opportunity is there. But it will require a few years worth of entering and points accumulation. Dont quote be on the time frame it will take to draw, but I think a safe range would be in the neighborhood of 3-8 years, dependant on the area and harvest goals set by the DNR. To many variables at play to pinpoint the exact amount of time. Safe to say start applying this December and every year thereafter. Back about 8 years ago, the bear estimated population was over 15,000. Today, it is closer to 11,000 which is very close to the DNRs goal.
Bear hunting infoJH45 & Esox lucias, help me out here.