Options for payout of unused vacation when retiring

[Moneymatters]

I'm leaving work(well retiring) and have the option to get paid for unused vacation. But I'm unsure what's the optimal approach..

Each day is 1/260th of annual salary. It will be 40 days leave. I'm not sure what the smart move is here or if there's another option I haven't considered..

Option A. (My current plan.) Request the amount be added to the retirement allowance for favourable tax treatment and keeping it outside of social insurance/pension deductions. is this feasible?

Option B. Get paid as a bonus. I suspect this is what will happen and I'll see less than half of it. But at least it will generate a pension contribution up to the limit I suppose..

Option C. Request they extend my last day of employment? Unattractive as deductions will be as high as now and insurance is actually higher than it will be with keizoku hoken once I'm unemployed... Are their other benefits to extending the final employment date?

Option D. Pull forward my last day in office by 2 months and use all vacation in one go. Sadly this isn't really viable as I have a bunch of things to accomplish to ensure a smooth transition of the hankos in turn linked to receiving some future payments..(Basically the backstory for John Wick if you are familiar)..

Option E. Relocate immediately to south America to begin a new life as "Kittie" in a Burlesque bar. (Added for completeness)..

[Kiro]

I have used Option A in the past, so it is definitely feasible... if the company agrees to it.
It indeed had a favourable tax treatment, and no social insurance/pension deductions whatsoever.

I have also used Option C in the past (different company), and social insurance was deducted as normal, but it had the advantage of "keeping me employed", which helped when looking for a job (I was able to say I was still employed and not "in a rush" when negotiating with future employer).

I like option A better now. And if you're retiring, then I'd definitely go for Option A.

[Moneymatters]

I have used Option A in the past, so it is definitely feasible... if the company agrees to it.
It indeed had a favourable tax treatment, and no social insurance/pension deductions whatsoever.

I have also used Option C in the past (different company), and social insurance was deducted as normal, but it had the advantage of "keeping me employed", which helped when looking for a job (I was able to say I was still employed and not "in a rush" when negotiating with future employer).

I like option A better now. And if you're retiring, then I'd definitely go for Option A.

thanks. Great to know there isn't a reason for them to reject option A! I'll push for that.

[William]

I believe that labor laws generally discourage companies from "buying back" unused paid holidays due to the potential negative consequences. While it’s not outright illegal, a company that does this frequently could face issues, as it might be seen as harmful to employees' well-being.

Although a company might agree to compensate for unused leave, they could also take the stance that employees must use their remaining days before their last working day—or risk losing them.

[runmanTX]

I would like to congratulate you on the retirement. I am jealous as I'm not quite there yet. A little bit further to go.
Any big plans now?

[Moneymatters]

I would like to congratulate you on the retirement. I am jealous as I'm not quite there yet. A little bit further to go.
Any big plans now?

Thanks! And thanks for the question. Writing about myself is kinda my thing..

Firstly, I’m hoping to sit down and just have 5 minutes to myself..

Whilst I’m not famed for planning, I did sketch some ideas here.
viewtopic.php?t=3609

Not much has changed since then. But I did convert a tatami room to flooring at the in-laws recently. (This elevated me to god like status among the natives..) Finally bought a nail gun! My wooden headstone will simple read “wish I’d bought a nail gun sooner” (written in nail heads..). I do enjoy the whole DIY process from; wandering the aisles of the “Pro” home center to standing back and admiring the completed project. (Less so the awkward stuff in between.)

Will probably rebuild the deck with fake wood and install secondary windows in our house whilst actively looking for a “fixer-upper” property.. I’ll do some domestic cycle touring with an eye on a potentially longer tour outside Japan next year.