I was referring to the round preceding the Round of 64. If you have 20 byes for the Round of 64, you have 44 spots open - hence 88 teams playing in the previous round (teams 21-108, if seeds hold to form). And you're right, any sub-50 team could easily lose to a team in the 100's. Wouldn't be surprising at all. A tournament that inclusive is going to look a lot like a tennis tournament, where you have a boatload of upsets in the 1st and 2nd round. So again, I don't know if there would be a substantial advantage for the pathway of a 1 seed and 5 seed. A little advantage, yes, but not quite like the traditional tournament. It greatly diminishes the importance of the regular season, especially when everyone is guaranteed a trip to the big dance.
That being said, there really is a limitless number of permutations for how the NCAA could format the tournament with some 346 teams. Perhaps the OOC and conference tournaments are nixed altogether... and everyone is sent into a regional bubble to vie for a round of 32 slot. Mark Emmert mentioned a couple of months ago that 32 teams would be more manageable. So, you could have 32 bubble-type tournaments, consisting of 10-11 schools, and the champion from each tournament advances to the NCAAs. They could arrange the tournaments so that no group has two schools from the same conference. Will be interesting to see if the NCAA actually entertains the idea that the ACC is pitching. Curious to know the vision of how the tournament would look.