Kevin is a gamer and slacker. His route requires Intelligence (to relate to him) and eventually high Corruption.
Once you have the Office Assistant job, money stops being an issue. Your focus should shift entirely to stat grinding and Corruption.
Do not skip the daily chore mini-games or opportunities to earn money. Purchasing gifts from the shop is mandatory for breaking through relationship plateaus in the mid-game. If you need help with a specific choice point, let me know: Which day or act you are currently playing The specific character route you want to pursue
