HeartLand and Legend are products of MIDEX management clones. Each airline can claim 3 former-MIDEX executives each. These are high caliber, high energy individuals with a lot of business savvy--especially the airlines.
The biggest hurdle for Heartland will be developing a market, and we had this discussion earlier. DAY could be a hard-case, but if the airline develops loyalty with the business people--it could take off. YX capitalized on MKE hometown loyalty over the years and became successful. To be honest, a lot of people didn't think that non-flamboyant MKE would support such a "fancy first class" airline in YX, but it worked. Then again, YX had Kimberly Clark bankrolling it for years.
Second issue. I hope that the 717 was the right choice of aircraft. There is all this hype here on the board that "new is better", but maybe an older model airframe such as the DC-9 would have made more sense. The -9 is not a mx hungry aircraft--contrary to popular belief, and is extremely reliable. Acquiring one outright is not at all cost prohibitive, and leasing is a very inexpensive option.
I am not sure what the terms on a 717 lease will be, but I'm sure it's not cheap. If you look at an example, Vanguard also attempted to start up with newer 737s and look where it is now--fighting for its very survival with older 200 series.
Last issue is purely a tangential one (and I'm good at those), since you raised the question.
Politics played a role in YX's decision to come into DSM. Tom Harkin, a very influential senator was thrilled to death when YX announced it would start jet service in DSM after Access went belly up. The problems arose when slots were awarded into DCA. As it turned out, only one non-stop into DCA from DSM was awarded. As you know, that doesn't make much business sense. Most everybody in business wants to return the same day. As it stands now, the only non-stops from DSM are to MKE and IND--with connecting service to LGA. There won't be any more significant movement in DSM until more slots can be acquried and aircraft freed up when MCI kicks into business. You won't see a mini-hub in DSM, but IND is becoming a focal point.