Advice on starting a small online business in Japan: sole-proprietor first, company later?

Hi all! I’ve been living in Japan for almost 10 years and am testing a small online service with a friend (nothing live or public yet). To keep costs low we’re thinking of opening first as a 個人事業主 (sole proprietor) under my name.
If the project gains traction we’d like to switch to a structure that lets us share ownership and profits, a GK (合同会社) or KK (株式会社).

A few questions for anyone who’s done this:

  1. Are there any tax or paperwork when you move from sole proprietor to GK/KK later?
  2. Besides the higher setup cost, is there a downside to just starting as a GK from day one?
  3. Any bilingual accountants or bookkeeping tools you’d recommend for a small online business?

PS: Not looking for formal legal advice, just personal experience. Appreciate any pointers!

by fmatsuo

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