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I think you need to ask yourself what are the "benefits of Madison" you want to take advantage of. If it's the coffee house/indie music/club scene, then any of these areas are going to feel far away. If it's the city generic entertainment/shopping benefits (movie theaters, malls, restaurants), then you may be able to find the same things in Janesville.
You are going to find home prices in Stoughton to be 20-40% less than Madison. Of course you need to figure in gas costs. Janesville and Milton have very affordable housing and are much closer to Beloit. Beloit itself is a quirky mix of demographics for a city its size. You can buy a fixer-upper in Beloit for $30-50k, but you may not be in a very good neighborhood. You won't be able to find a fixer-upper in Stoughton for under $100k, and that's going to be a major project.
Again, I think you need to ask what benefits you want from Madison and whether it is easier to commute to take advantage of those benefits when you want them or whether it is easier to commute to work everyday.
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