It's an interesting question. Certainly no "right" answer.I don’t see much chance of it almost any year - that’s why it would be a special season... although the way the roster is shaping up, it looks like ‘20-‘21 Iowa could have a substantially more experienced (and hopefully better) team than ‘19-‘20. JMO
There is a valid argument to be made both ways. Admittedly, my vote (Option B) is subject to a lot more risk in terms of people going pro or transferring - and having a completely different looking roster than what it looks like it’ll be right now - than Option A, which is a big drawback
While my vote is for play now if at all possible, there's little guarantee that having Bohannon this year results in a tourney bid let alone something beyond that.
If things fall into place in the best scenario, I agree with you that the 20-21 season looks like it would have more potential.