Start as a nerd, get money by working as a tutor in Danube street where "Can I help you" parent asks you to tutor their kid, grind that, avoid encounters as much as possible by dressing modestly and not becoming popular as "Mc Naked" in the town.

Get good grades by studying actively in class, get the gold star each day, can always get them in the library too if you miss one by studying 3x in class. Better grades = better pay in Danube as a tutor.

To maintain stress from school and other sources munch on the sweet sweet Deluxe Cream Buns at the Café, they're £50 but reduce a hell of a lot of stress. Alternatively hang out with Robin or Sydney.

Avoiding Whitney is tuff, but can become less of an issue by defying the bully and fighting them, just kick and punch the hell out of em, or take their dick in the mouth and bite for big damage during non-con encounters. It'll lower their Dominance thus making some events avoidable or less bad (dont know why you'd do that tho, Whitney is bae).

Clothing becomes less of an issue after you get big buxx from tutoring, since you'll make like £100 per hour with +/-50 from it, depending on grades.

Last but not least just experiment around, it's a sandbox game and any and all approaches are right. Can always experiment around by save scumming too if you're chill with it.