A codebase that's actively growing, has multiple contributors, and has already had real bugs traced back to null/undefined handling or type confusion — strict mode pays for itself quickly there, because the errors it's catching are the exact bugs that already cost you debugging time.
A small, stable codebase with one maintainer and no active bug pattern around typing issues — the migration cost is real and the marginal safety benefit is small. This is a "when you have time," not "do it this sprint," situation.
Enable strict mode only for new files via a per-directory tsconfig override, then migrate existing files opportunistically whenever you're already touching them for other reasons. A big-bang full migration is where most of these efforts stall out and get abandoned halfway.