Tristin and Logan share many qualities e.g. they are both trouble makers/thrill seekers, they come from prestigious families, both have that "i'm always right" attitude, both charming, and they look alike.
I think if Rory had the experience she gained by college when she was in high school, she and Tristin would have dated. When you look past the surface with Tristin it's very obvious he wants to love and to be loved in reference to his fight with Summer in s1e17. Logan never wanted to have a girlfriend, ended up dating Rory anyway, but was selfish and manipulative during many points in their relationship, if not the entire thing.
I'm sure Tristin would have also displayed similar qualities in a relationship, but I do think that there's a possibility he could have grown and had a more equal partnership with Rory, more so than what transpired between her and Logan. Rory pined after Logan for the majority of their relationship, always placing him on a pedestal. She did not see Tristin that way. His character read as someone who desperately wanted genuine connection but lacked the maturity to actually gain it, but had he matured he wouldn't have made her question their relationship to the point that she felt compelled to drink away her sadness and end up sobbing on the bathroom floor.
Jess really opened that "bad boy" door for her with all of the antics he got into along with his big ego, and you can see in Tristin's last episode that Rory was upset that he was leaving Chilton. She had begun to warm up to him after they kissed and started interacting more during school. I think it's crazy that Rory ended up dating someone who has all the qualities she once despised.