How to Do a JS to TypeScript Conversion
How to Do a JS to TypeScript Conversion

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How to Do a TypeScript Conversion — Sympolymathesy, by Chris Krycho

How to Do a JS to TypeScript Conversion
How to Do a TypeScript Conversion — Sympolymathesy, by Chris Krycho
The loose approach could be good as a way to get your feet wet if the entire team has no preexisting TS experience and needs to get weaned into it.
However when it comes to seriously converting the codebase I completely agree, not just for TS conversations, but for all major refactors. Slowly updating the same file over and over again is simply inefficient and leads to things never fully getting done.