Your friend will like MSN a lot. I am a fifth generation Madisonian and having traveled all over the US and Europe, I still find that this place suits me. Housing is not cheap here, especially homes (I paid 250k for my 2 bedroom/1 bath 1300 sq ft house last fall), but if you look around a bit decent deals can be had on apartments. Overall, there's a lot to do if you have time outside of work and it will rarely take you more than 20 minutes to get from one side of town to the other.
As to your friend's efforts to sustain his romance, he should join NWA's WorldPerks frequent flier program. He can maximize his miles by not only flying NW (or any other SkyTeam member - DL, CO, KLM, AF), but signing up for their check and credit cards through US Bank, cell phone service, etc. Check out
www.nwa.com for information on that stuff. Also a
great site for more detailed frequent flier information on all airlines is
http://www.smartertravel.com/ff/FlyerTalk/ Some of the members on there are a little out of control on the FF stuff, but you can often find answers to questions very quickly, as well as great insider tips.
NWA flies from MSN to MEM direct, using NWAirlink metal that arrives at MSN around 930ish at night and then heads back down to MEM at about 630ish AM. Depending on the season, it's either a Pinnacle CRJ (about mid-May through mid-December) or a Mesaba Avro RJ 85 (winter and spring). I prefer the Avro because its cabin is wider than a DC-9 and it has 12 first class seats. If NWA's fare to MEM direct is high, DL flies there from MSN through CVG, or CO through CLE. He will be able to earn NW FF miles flying either.
As to MKE, it's an easy 70 to 80 minute drive from MSN and NWA itself flies most of the flights to MEM. Also, if the MSN and MKE fares are killer (which i I have found is rare) he might want to consider ORD. It's about a 90 to 110 minute drive assuming a bit of traffic, but I personally will not fly through there due under any circumstances to the high frequency of delays.
Feel free to PM me if you or your friend need any more information.