Advice on how to deal with leftover PTO when changing jobs
I'm in the process of switching jobs, and at my current job I have over 25 days of PTO left (~5 work weeks). The new job wants me to start in ~6 weeks. Before leaving I would like to do a proper handover at my current job since I know my leaving will leave quite the hole in the department and is most definitely going to add to my coworkers' overtime - in other words, I don't want to hand in my 30 days notice and immediately go on holiday until the day of my resignation.
What can I do in this situation? Ideally I'd have it paid out, but I heard that in Japan that's basically impossible. I suppose the second best option is just finishing my handover and then taking the rest of my PTO, and letting it overlap with my new job - but is that legal? I read on this subreddit that it might cause trouble with taxes/health insurance/pension, but is it doable? Is there anything I can do to get my current company to do a payout instead?
Technically I could ask the new job to delay the start date a bit, but they've expressed that my start date would then fall into the company's vacation period, and the hiring manager wouldn't be around for like 3 weeks during that time
Any advice is appreciated