Update: I showed my cousin in Dallas 3 logo redesigns last month and he picked the one I hated
The clunky dated version with the heavy serif beat my clean modern one because he said the new one looked like every other app on his phone, which made me rethink how sameness is the real brand killer.
Did you ask him why the old one felt right to him, or just take the win for the clunky one? Because that answer is the real gold here, and it's usually something dumb specific like "this one reminds me of the sign at my gym" or "it looks like a real company, not a startup." When I did logo work for a buddy's shop, the version I hated won because it matched the sticker on his truck, and honestly that beat every good reason I had. My tip is to make three new rounds where each one keeps some of that dated, familiar feel but cleans up the worst parts, then let him pick again. You'll usually land on something people trust and that doesn't look like every other app icon on a home screen.