It's impossible to say. Two schools can check every box, but one can just check the boxes and the other can blow you away. These are factors and its all entirely subjective. Where one get a check, another might get a check +.
Winning is nice, but I wouldn't get caught up in it. Would you pass on a Va Tech, Pitt, Notre Dame to go to a winner in a weaker conference? Would you pass on a Fullerton or a Long Beach because they had a few down years? I would worry more about the level of play than I would the record. Go to a game and watch. I can guarantee a lot of middle of the road and teams with losing records are better than a lot of 30 win teams in weaker conferences. If you're choosing between two schools in the same conference that you're 50/50 on, then maybe culture and win % come into play.
For me, I'd want to play the best competition possible. To me there is a difference between a 20 win team that is competitive and a 20 win team that gets spanked 2 of 3 every series. You have to be able to read the room. You can look at a 20 win team and say "yeah but look who they're playing" and you can look at a 35 win team and say "yeah but look who they're playing". I'd consider win %, but I wouldn't let it be a deciding factor.