[KirinDave]

If your priority is "ingratiate yourself to your manager" then yeah, it's best to pick small superficial problems or prefer patch-job fixes. These decisions tend to be informed by how much technical debt the "short" fix makes.

But if a problem genuinely will take 6 weeks to solve, then it's probably a worthwhile problem to solve. Those sorts of problems tend to have far-reaching implications for sites and their ability to scale. The big question is when to solve it. Competent engineers know when to do this.

Managers who can't see this? Bad managers. Bad managers can kill a startup just as effectively as 'rockstar' engineers.