Other way around, you get more house for your money in downtown Kenosha. Northside especially. I live in Paddock Lake, which is about 10 mi from downtown, I like it here. But my parents casually look for real estate we can't afford

and we're amazed at how much cheaper Kenosha houses are. Also, I generally discourage homeschooling; pretty much all of the schools in the area are excellent, especially Westosha Central High School, west of the I in Paddock Lake, which is always on Newsweek's best schools list.
You really don't have to worry too much about crime in this county. It's not bad. Pretty much any neighborhood is safe if you lock your doors at night. I would even look in Harborpark, which is a bunch of condos in a beautiful park on the lake with easy streetcar and bus access to downtown and the train station, which can take you to Chicago, and (by 2011 probably) Milwaukee.
Somers is also good for the conveniences you listed; you'd still drive to Woodman's (as you would anywhere in the county; PL's SuperValu is too small and comparatively expensive) but you do have WalMart, Sam's Club, and a future Milwaukee train station.
All in all, this is a great area, and most of the towns would be a safe bet. (I personally dislike White Caps because, in my opinion, it's terribly ugly and all the same. Also, home values are a little inflated for the size compared to the surrounding neighborhoods. Most of Salem (not Paddock Lake, they are different even though Paddock Lake has a Salem address) is like that too)
Speaking of which, if you choose to live in Westosha (the county west of I-94, as opposed to The City, aka Kenosha and suburbs Pleasant Prairie and Somers), you will have to get used to the weird addresses:
* Brighton has no post office and is split between Salem, Burlington, Bristol, and Union Grove address wise.
*Paddock Lake is a village, not a city, within Salem Township, and has no post office. Silver Lake is a similarly sized village in Salem Township which is in a completely different school district and does have a post office. Go figure.
* Paris has no post office and practically no taxes (!), but, like Brighton, is in the middle of nowhere. It just happens to be a nowhere which is closer to the amenities of both Kenosha and Racine. It has no post office and is split between Somers, Union Grove, Bristol, and Salem address wise.
To address some peoples posts:
City414- ??? I'm pretty sure no one considers it a full-fledged part of Chicagoland. Kenosha is tied pretty heavily to both Chicago and Milwaukee. It's definitely not a "suburb" as we would think of it.
lola76- I lived in Brighton for 2 years before moving to Paddock Lake and don't regret it. But, I do admit to using the good Lord's SCHOOL CHOICE PROGRAM (!) to go to Brighton Elementary instead of Salem. But paddock lake has much more much closer than Brighton did; PL has some semblance of a downtown, we have a grocery store and a cafe and some restaurants and McD's and Walgreens. Brighton is a town where people measure distances by cornfields, but in PL we measure them by blocks. PL is cheaper but still decent.
Everwinter- Hehehe. I caught it. You can tell which house the helicopter one is; it's brick now. I guess they were kind of like "hey, if we get another helicopter, we SURE AS HELL aren't dealing with this siding crap. BRICK IT IS!"