I would spend some time on the question of why you want to move to the Indy market.
The money certainly isn't any better than South Bend. The pay gap between larger and smaller markets keeps getting smaller and smaller. In fact, being a big fish in the Michiana likely affords you more opportunity for remotes and endorsements than you'd get as a part-timer in Indy.
If it's to build your resume or climb to an even bigger market [Chicago, Detroit, etc.], it may not be necessary or helpful. Similar to the money argument above, South Bend gives you a better chance to dominate demos in a better daypart than what you will get in Indy. There's merit to a long track record as, say a #1 AM Drive show for three years in South Bend versus languishing in 11th with Nights in Indy. Stability and success can take you a long way.
If it's to be closer to family or friends in Indy, I can't argue with that. However, if your loved ones are in South Bend, Elkhart, Niles, Cassopolis, Bremen, Plymouth, etc., stay there. Geography and proximity are bigger factors to your happiness/sanity than market size is to your career.
If it's because you think "that's what I'm supposed to do," know that it's just not that way anymore. The "traditional career path" is long out the window, much as it is in other professions. "Market-hopping" to "climb the ladder" just isn't a requirement. Hone your skills; be compelling and entertaining; build your professional network; and learn every aspect of the business. That's the best recipe for growth in your career.
You make a great point, but it is becoming more and more apparent to me everyday that there is just no room for growth in South Bend. You have AMP who is having there fair share of problems, and you have got Fed Med who won't even give you a second look unless you are a 5+ year Sales God. My career path has actually started to go backwards instead of forwards. There's just no opportunity to prove, and continue to improve, myself in South Bend. And trust me, it's not about "Market Hopping" or even about money. I'm single, very little debt, no children to support. I've been in this business for 10 years, and I still want to learn, and grow, become the absolute best I can be, and...God Willing...one day pass what I have learned on to the next generation, but in my current situation, that's just not happening. I feel that getting my foot in the door in Indy will allow me to get a fresh start, re-invent myself, grow my professional network, and the rest I will leave up to the "Big Man Upstairs".