If a degenerate like Arthur gets to have a happy ending in GGGB, then I'm pretty sure that any main character in ORS will get to have one. It's how Eva rolls. The variety of choices is what makes her games shine.
Breaking up Cindy and Wade is a 'bad' choice if Ian is a well-adjusted adult, a loyal friend, or a soy boy like Perry. I play him as a nasty, physical beast, an unapologetic high-functioning psychopath who doesn't give a fuck about bums like Wade and Perry. From his point of view, a loser like Wade should be thankful Ian only kicked his fat ass out of his girlfriend's bed and hasn't low-kicked him out of existence yet.
In fact, my canon Ian isn't even that interested in Cindy after having slept with her since she's low-hanging fruit, and he's aiming much higher. He wants to demolish Ivy's emotional barriers with his slightly above-average cock, make her fall in love with him, and crash at her pimped-out pad, sticking his beak in that stalkfap/hush-hush escort money. Or even better -- pressure Minerva into divorcing her cucked husband and giving up custody of her son so Ian can move in with her and drive around in the black SUV.
Knowing Eva's previous work, I'll be disappointed if by the end of the game, Ian doesn't have the option to make his Pulitzer acceptance speech high on coke.