I think if you get a lot of teams selected, it speaks to depth - but if you get a lot of teams that move forward, it speaks to quality/strength at the top. Both should be considered.
There's the "steel sharpens steel" argument that going against tough opponents makes you stronger, so deeper conferences should have stronger teams at the top... but if you aren't consistently showing up in the Sweet 16 or Elite 8, it's hard to make an argument that you're one of the top conferences in the country.
Last year the Big Ten got 1 to the Sweet 16 and none to the Elite 8 (2 teams seeded 4th or better). The prior year, 2 to the Sweet 16 and none to the Elite 8 (3 teams). The prior year, 1 to the Sweet 16 and 1 to the Elite 8 (5 teams).
Out of 48 teams in the last three Sweet 16s, just 4 have been from the Big Ten, despite there being 10 seeded 4th or better. Of the 24 teams in the last three Elite 8s, just 1 has been from the Big Ten (despite there being 5 teams seeded 2nd or better).
At the end of the day, the Big Ten needs to find ways to succeed at the end of the year.