Is this a feasible plan?

information:
I am a 26(M) Singaporean, I work in a japanese firm for HR in singapore. My japanese proficiency is conversational(I have no issues communicating at work entirely in jp to my jp bosses/colleagues, though my writing is much poorer) and I am self-taught so I have not tried applying for jlpt yet(though i intend to after practicing some more)

I've recently started planning for my future and I really wanted to try getting a working visa for japan
(Excluding hitting the lottery of getting intra-company transferred or getting a spouse visa)

My ~8 year plan would be to move to japan before im 35
I currently do not have a bachelor degree and while it isn't completely out of the book, it does seems unlikely that I'll get a bachelor degree in singapore (there are only 6 recognized universities in singapore, getting in will be a challenge when i'll be 30)

My current plan is to continue working for japanese firms in sg while getting certified for jlpt n2 and

1. get 10 years of professional experience, get promoted to hr manager for a japanese firm / any senior office positions and try to apply for jp working visa with jlpt n2
2. *edited to remove this*
3. save up money while working right now, get jlpt n2 and apply for student visa for a bachelor(probably in eng and not jp) and hopefully managed to get employed for a working visa
4. save up money while working right now, get jlpt n2 and apply for student visa for a bachelor(probably in eng and not jp) and applying for JET program as a last resort to experience working in jp (I'll probably get a bachelor in hr, finance or marketing)

I am excluding any possible intra-company prospects since those are luck based on whether the company even has/plans to transfers so thoughts on plans 1,2,3,4?
Is it feasible for any of those plans to succeed or are my chances impossibly slim due to my field or is it a "get a local uni in my country or bust"