Behind Maya/Josy I feel Sage has the most drama to deal with regarding Quinn and the rest of the HOT's. The MC/Jill/Bella triangle isn't worrying in the slightest bit so far in the story, Bella is continuously reacting to Jill's positive comments about the date with MC positively. The drama is more Bella's side than Jill.
For me, as the MC, Sage offers the least drama for two reasons. The first is because I don't consider Quinn and the HOTs to be an issue. I am not a part of that fraternity and hold no responsibility for how it's run. The second is because I don't consider Chad to be a threat. On the Sage route, as unethical as it is, she suggests and initiates most of the interactions with me, which are initially lustful but increasingly affectionate. If not on the Sage route, she's still in the picture, such as in the last update where she hints at wanting something to eventuate between us. If it were not to work out with Sage, I wouldn't be too affected, as there are other options.
I'd say that the pairings of Maya / Josy and Jill / Isabella offer the most drama because any mutual romance that develops between the MC and any of these four may create some friction between the pairings. Maya and Josy, as a couple, may have unresolved issues. Jill and Isabella are both secretive and, while they may not blatantly lie to the MC about things, they are careful about the truths that they share with him. Avenues with both pairings are mental and emotional minefields.
I also think that the energetic and jovial interactions between the MC and Sage are natural and the least draining. The MC is himself around her. She knows it and not only accepts it, but enjoys it. They're not walking on egg shells around each other; their connection is natural. This for me is fundamental and already a big plus. I look to see if tension and chemistry are present in a budding relationship, and both are evident in their moments together.
Next to Sage, I'd say that the interactions with Jill are generally positive and authentic. She's older and from a different social class, but she's actually curious about the MC and drawn to him. If you consider tension, it's there. The chemistry is there too, as they are not only destined professionals, but they are also both into music and sports. I'd also add that she doesn't appear to want to change the MC. One of the best moments for me in the game so far is when the MC gives her a black eye with his dildo helmet, in her bed, and she doesn't have a meltdown. Top moment, for sure.
With the other big three love interests, I think that the potential for drama is greater. There is simmering tension with Isabella, but she corrects and lectures him a lot, which could be seen as a bit of a red flag in the early stages of any bond or relationship. Maya, I believe, is trying to shape him into someone she'd ideally want to be with; I can't forget how the MC must pass her seemingly insignificant tests during that lunch or how she sells him the benefits of a feminism class. Could the MC really be himself or develop his own and even slightly edgy identity around these two? I'm not sure. With Josy, I think that the drama really comes from her past with Maya, and the possibility that they have not overcome any past problems or differences.