Student Visa to Part/Full time Visa worries

Hello Everyone and thank you for reading/commenting on this!

Preamble:
I am due to attend a language school in Osaka beginning in April. I have been living in Taiwan for the last seven years and have permanent residency. My current student visa is for Japan is due to be issued in early March. I would like to leave here in early March but the school was saying that it could be a problem, because they give you exactly how long the course's tenure is on your visa. In my case it's fifteen months.
My questions are:

  1. As my course is fifteen months, and the visa – from what I've read – is capped at two years. Even if the graduation period is in late March, I should have many months available extension to see this out. Is this correct?
  2. I have enough savings to last two years but I would like to find a part time job within this period*. There's lots of conflicting information, so I'm unsure as to how difficult the student to work visa transition is? I've read about people being part time then graduating and going full time, presumably with an offer in hand prior to graduation. I can go back to Taiwan if needs must when renewing/changing the visa but I'd just like some clarification. Thanks!

* I understand my attending the language school in the morning may affect which jobs I can do as most (salaried)sales positions are a full time biscuit; I may work in a different field temporarily.

P.S. I have more than a decade of professional experience (manufacturing sales, account director) and a bachelor's degree. I also speak Chinese but my mother tongue is English. I was hoping to find a job in manufacturing sales, which is why I chose Osaka over Tokyo. The current company I work for does want a sales manager in Japan but I'd not like to rely on that given it's a hassle to setup ltds/power of attorney/IP in new places.

by sliceandtight

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