I'm on vacation at the moment and pressed for time. I can try to expand some of thoughts when I return to town. I used to live downtown and now live 25 miles south of the city in Franklin. When I lived downtown, I did a lot of club rides that I either drove or rode to. Most of my cycling friends lived in or near Broad Ripple--about 7 miles due north of downtown. From there, we mostly rode northwest or northeast. It wasn't hard to go in either direction. Living downtown also gave me easy access to southsode rides. So, while I did have to travel to most rides, it rarely took long.

From where I live now, I can ride from my door. Problem is that I'm cut off from a lot of other things. I rarely go to club rides anymore. The only plus is that I'm within 45 minutes of Brown County's mtb trails. I started mtbing this summer so when I lived downtown, that wasn't an issue.

In my opinion, you can road ride from most places in Indy with a bit of effort. For me, what side of town to live on would depend on a handful of other considerations, cost of living and congestion among them. Access to good trails adds another element into the mix. While there are other trails, I'd sure want fairly easy access to Brown County. I know i'd personally move back downtown in a heartbeat. With no commute, I just had so much more time, and the interstate and major arteries made it so easy to get everywhere.