i think its pretty clear - for virtually any situation in d2/d3, being in a super conference makes it harder to build top tier programs and harder to win championships. but, its also a heck of a lot of fun, when conference achievements are a big deal and you get those rivalries going. so many regular seasons are boring, but when you risk going 9-7 with a borderline top 10 team because you auto piloted through conference, seems to really spice things up.
so, i think it just comes down to what people are looking for, if you are trying to move up, or really focused on some objective, it may not make sense. if you are looking for a long term situation or want to get better as a coach, its great. all that said, i think its really stupid to consider pulling bonus money for d2/d3 conferences.
i think you are OK not asking oldave - most people want fuller conferences, and folks trying to move up quickly won't be around long enough for the new folks to build their programs up, anyway. i think its generally appreciated when people go out and make some effort to fill spots, never heard of it being a problem.