Should the NCAA expand March Madness to 96 teams? There are a couple ways to look at this, first would be which teams would get the benefit, second would be what's the use as there will always be teams that feel left out so is it really necessary, and third would be is it just a way to get more money. The answer to the last question is the easiest of them all, of course it is. Money is the same reason the BCS system exists in football and not a playoff.
So with the last question answered lets try to answer the other two. There is no way to tell if any of the smaller conferences would be able to get any extra teams in the tourney especially when the committee goes off of RPI, strength of schedule, and conference rankings that are, to a degree, guess work. There is no way to tell the difference between a team that places out of the top 5 in a power conference and a top 3 team in most of the mid-major conferences. The strength of schedule for a power conference like the Big East or ACC will always be better then the majority of the mid-majors because they will have more top 25 teams. But this is also guess work, just look at how many number 1 teams have fallen in the last month, so that isn't the best way to judge the teams. If you go just by won/loss then the power conferences will cry fowl because they say they play more games against "tougher competition," but is this really true?
Let's take Syracuse which is ranked number 3 right now, their non-conference schedule included 4 games against teams in the top 25 and 8 games against teams with a combined record of 81-92, this includes one team that is at the top of their conference. Syracuse's strength of schedule is 9 right now, their non-conference opponents best RPI is California's 24, but includes 7 teams with an RPI of 144 or higher. Cornell, which was one of Syracuse's opponents has a strength of schedule of 138 but played only 6 teams with an RPI over 144. Of course the I am not saying that the Big East and the Ivy League as a whole are comparable top to bottom, but could Princeton or Harvard take out a team in the tourney? How about Cincinnati, right now they are number 6 in the Big East and is slated as a bubble team. Of their 12 non-conference games 7 of them had an RPI over 151, they went 2-3 against the 5 that were under that RPI number.
To further illustrate some of this look at the Pac-10. In several brackets they have 2 teams going to the tournament, in the same brackets the Big East and the Big 12 have 7 and the ACC has 6, are Maryland or Cincinnati really that much better than Washington? Washington has 4 non-conference games against teams with an RPI over 151, Cincinnati had 7 and Maryland had 6. Yes, Oregon and Oregon State are bad and bring down the Pac-10 ratings numbers but Boston College is not much better and the ACC is not hurt as much by it. So back to the original point that all of the numbers are subjective once you get past the top 4 or 5 teams of a power conference, when you play a conference game at home you have a better chance of winning as the crowd is goiong to be louder and more obnoxious.
As far as school's being upset that they get left out of the tournament...who cares, that is half the fun. We all love to argue about stuff and why not have something that starts an argument with no clear answer. The field was expanded to 64 because there was so much parity that more teams needed to get the chance to play. The best way to make 96 work would be to make it so that if a team wins the regular season they are in and if a team wins the conference tournament they are in as well. That would legitimize the move and also allow more teams that should get in and don't make it. Also the teams that normally play the number one seed would change, as adding 32 teams would give the top 16 seeds a buy in the first round and therefore those weaker conference teams may actually have a shot of winning a game in the tournament.