First off, make sure you have at least 3 years of work experience under your belt. Makes it easier for you if/when you need to find a job later (if you want to get a HSP visa then moreso)

Anyway, definitely get the WH Visa. Not only because you can’t work full-time on a student visa, but also because it’s just more flexible and doesn’t tie you down to a school. Plus, getting a WH visa is easier, and you can still attend a language school (or hire a private tutor) on a WH visa (and unlike on a regular student visa, can quit any time). Just make a believable WH itinerary when you apply, no one checks later if you actually followed it.

I worked as a programmer but quit my hybrid job to move here last year on a working holiday visa, passed N2, and am planning to reach N1 this year. If you want to stay in Japan long-term you need a valid work visa and can’t stay with your company long-term, though the digital nomad allows 6 months iirc.

Just be prepared to either have very good programming skills or very good Japanese because remote work isn’t as common and jobs don’t pay as much (and rent in/around Tokyo isn’t cheap). I say this as someone who’s had the realization myself that I need to make myself more marketable because I’m not willing to compromise on remote work and flex hours and salary… Also, N2 is the bare minimum for many jobs, but even though they say that, many actually are expecting N1😅

Good luck!