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Because Dean started off as a "good guy", Jess was a brief dalliance and wasn't explored enough, whereas Logan represented the affluent part of society which Lorelai made a point to run away from and in turn people didn't want Rory with someone like that, they wanted her with her own version of Luke.
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I think, it was more than that.
Yale Rory is just not as successful and confident (or even as moral) as high school Rory. People could associate that with Logan, but that's not really his fault. She was less confident in her first year of Yale too and she even slept with married Dean at the time.
Rory is just not as sheltered and admired by adults as she was in Dean's and Jess's time. Competition in "real world" is much tougher.
I just wanted to point out that Rory and Logan were really buddies beside being lovers/boyfriend, girlfriend. It wasn't a traditional romance with traditional male and female roles and rules about monogamy at the beginning. In the beginning Rory was chasing Logan and not vice versa. It's great and liberating - but the question is, whether Amy ever intended to change their dynamic and allow them to be a "traditional couple". Maybe living together yes (in 2017 for example after divorce from Odette), but not really married. It's hard to read Amy though.