As much as we should root for the conference, I think I'd rather have three teams with better seeding in the tourney than four or five that all get bounced right away. Looks like Dayton could make serious noise in March; best thing (aside from Mason winning the A10) would be Dayton winning regular season and tourney to get a good seed.
I don't know...I think more bids gives you more opportunities to advance (4 teams in is equivalent to one team making the Elite 8 money-wise -- units are units). The MVC in 2006 got more money than the CAA despite our Final Four, because they had two teams in the Sweet 16, 4 teams overall (3+3+1+1 versus 5+1 for us).
The tournament is unpredictable, so seeding isn't necessarily a guarantee. Look at Dayton in 2016 as a 7 seed losing to a 10, but that 10 wound up making the Final Four. UVA went down to a 16 seed in the first round.
If Dayton is good enough, their seeding won't matter as much (look at our 11 seed in 2006, vcu's 11 seed in 2011).