As for good areas... if he gets a job in Milwaukee, Burlington, Union Grove, Racine, Kenosha... all are good places distance wise, and vary in size from fairly rural to city.

If he ends up in Chicago, and you want to stay just this side of the border, I'd look near Bristol, Genoa City, Pleasant Prarie, and Kenosha (still).

You may also want to consider just living in Lake Geneva or Elkhorn! It's a beautiful area, and you can hop right on the interstate. I think last time I went there from Milwaukee it took about 30 minutes, and I think it's not much longer to go to Chicago (though I've never tried)
Let us know what happens!

*hi-jack over*

*drool drool drool*

DIY... I live on Cass btw Kilbourn and Wells right now. Street parking is...well...not fun, although it seems to have gotten better now that the whole festival season is over (I envy your lot space during that Summerfest madness). I think you could probably get away with giving up your lot space until next summer, if you don't mind occasionally having to walk several blocks. Normally, though, I can park within 2 or 3 blocks of my apartment.

Unemployment claims to be one of the lowest in the country (I'm near Boston so it cant get much worse than here). I dont have any highly specialized skills, so I would be looking at reception/light admin jobs. How is the job market for that sort of stuff? I'm in retail now, but I dont want to do that full time (I'm only in it because of the job market here). I do have a decent set of skills and plan on talking to a temp agency or two to get a feel for the market, but I wanted to get a heads up before I take a vacation out there next spring. I also realize that salaries arent as high as they are here, but neither is the cost of living.

Also, I currently own a condo and I was looking to buy a place out there too. A search on Realtor.com brought up over 200 single family/condos in my price range (under $50K) I'll make enough money from the sale of my home to put 20% on a $50K home, pay off my car and credit card, and still have enough cash for moving expenses. A lot of these homes (mostly in between the $30-50K range) look fairly decent. It's just a bit unbelievable to me that there are so many homes that are so inexpensive. Is the market tough though? Is it a buyers market, sellers market, or somewhere in the middle? Will I be able to bargain down the price of these homes a bit or will I be caught in a bidding war? Will I be able to find a home in move in condition (not needing a bunch of work to bring it up to code). And the neighborhoods these homes are in - I realize they may not be the best but I dont see bars on the windows of the homes I searched. So could I find a place in my price range in a halfway decent neighborhood? Just a comparison, the homes I saw on realtor.com - put a 1 in front of the price and you get an idea of the market out here.

you might want to check crime indexes and things in the neighborhoods you're considering.... I can give you a slight idea about some neighborhoods, and if jessicazee is still on this thread she probably can also.

I think the job market is questionable everywhere right now, but its tough here. I've been submitting resumes like crazy and I got all excited the other day because I got a "thank you for your interest in the position" letter. Thats more response than I've gotten from most jobs.

My plan of action is pretty well thought out. Right now I'm putting out feelers, trying to get a bit of feedback on the place. So far I'm liking what I hear. Then, in the spring or when I get a bit of money saved up, I'll visit and get a sense of how I might actually like it there. I also plan on visiting a realtor at that time to do a preliminary housing search and see if it will go in the direction I want it to. I also plan on visiting a temp agency, possibly registering to be available at a later date, to get some firm info on the job market and my chances of being able to support myself. Then, if all goes well I'll make a second visit to put a deposit on a place and put the wheels in motion. But right now its too soon to contact the pros listed above because I dont have any firm dates and I dont want to come across as sounding to wishy-washy.

Riverwest (cheap rent and nice diverse neighbors; more and more homes are owner-occupied and new businesses cropping up - it's where I call home)

Downtown/Lower East Side (lots of warehouse being converted to townhouses; still no parking; convenience to nightlife & shopping; pretty safe)

Shorewood (high taxes, but lots of Art Deco apartment living & quiet)

Wauwatosa (nice city/suburb west of Milwaukee)

Unfortunately, Milwaukee still has a segregation problem. Most of the inner city and northwest areas have image problems, and absentee landlords, not to mention most of the crime in the city. Rely on intuition if you visit any places for rent/sale and notice the upkeep of neighboring buildings and gardens. This can tell you a lot about the values of a neighborhood, and whether you yourself would feel safe living there.

I actually (finally) registered just to be able to give you my perspective on this. First, Milwaukee rocks. Second, disregard everything you think you know about housing prices. This is a different world. My in-laws are aghast that a house just sold for $225,000 in their residential neighborhood in the city (similar to West Roxbury, let's say... it's in Story Hill, near the stadium, for those of you in the Brew). This is a large single family home, garage, yard, the works. (Again, for those in Milwaukee, a house like that in Boston would be ~$600,000)

Milwaukee is a wonderful city, and I would want to live their myself if I weren't in an industry that is specific locally. Great parks, museums, restaurants, etc.

My two cents on the restaurants discussed back over the summer: there's a Japanese restaurant on Brown Deer in Glendale that is pricey but excellent. There is a restaurant in the Third Ward that is a brewpub and has seating out on the river that I love. (You can see I'm not so hot with names...)