I assume the reason no extension happened last off-season is because at that time Crean still had 4 seasons left on his contract (through 6/20/2020) and Glass saw no need for an extension then. Once this season's over, Crean would thus presumably have only 3 seasons left and that's why I expect an extension next spring in order to "help him recruit."
Only way I don't see that happening is if Crean's team doesn't even get an NCAA tournament bid--and even then I wouldn't be shocked to see an extension. If it does happen, I hope to God it's not as extravagant and over-the-top as the last one, and that the $1 Mil buyout (after 7/1/2017 IIRC) can be reduced even further, maybe to $500,000. Not saying I like or agree with this scenario, only that I suspect it's the most likely one at this point in time.
And I'm unapologetically selfish about TC's hypothetical replacements--I'm not very interested in Nored, or even Holtmann, Mack, Jacobson or A.Miller. I want a "home run hire" that says, for maybe the first time in 16 or 17 years, IU Admin "got it right." Unfortunately, for me about the only guys who fit that category are Stevens, Donovan, T. Bennett and S. Miller, and I don't know if any of them would be genuinely interested. So IU either gambles on extending Crean or gambles on someone from the Holtmann, Mack, Jacobson or A. Miller category.
Also, from what I've heard, Gregg Marshall and Glass might not be a good fit, philosophically speaking. And GM's already making almost as much as Crean does, so I don't know how much ($4 Mil a year? $4.5?) it might take to get him interested. Not sure how he'd approach recruiting at a (formerly?) elite program like IU's, either.