But isn't there a limit on amount of cash top up to RA post creation of RA?
Yes, but my point is that you don't have a diversification problem -- putting "too many eggs" into the CPF "basket" -- if your total wealth is big enough. Merely have one owner-occupied home in Singapore and your total wealth is probably big enough to avoid portfolio concentration concerns. (Although I'd still argue for "reasonable global portfolio diversification.")
Thought this might be the best place to ask for help on this.
Not sure if it is IRAS or CPF specific actually, but trying my luck...
Situation:
I am Singaporean - an Australian company is trying to hire me in Singapore as first person on the ground so they are not very familiar with CPF and its' requirements. They do not have an entity in Singapore but have plans to setup once there is traction (revenue) coming from this market. They are paying in SGD
Problem:
1) They are not sure how to incorporate CPF and requested that I do it myself
2) I already suggested that they reach CPF directly to check for employer side but they insisted that I do it myself (implying that I would be a self-employed/contractor status)
3) Yearly rolling contract
Yes, from your description you'll be self-employed, assuming IRAS agrees. Thus you'll be required to contribute to MediSave but not to your Ordinary and Special Accounts.
Questions:
1) Tax implications?
None directly. You'll still pay income tax.
2) A typical employer in Singapore will just factor 20% [Employee side] into the salary, and 17% [Employer side] usually company's admin/finance will take care --- If company wants me to contribute to CPF myself, does that mean they need to include all 37% of CPF into my salary, and thus every month I contribute accordingly myself as a self-employed?
No, but the fact this Australian company won't be contributing their 17% -- which could be as much as S$17,340 per year if your monthly salary is at least $6,000 and your variable pay (bonuses, commissions, etc.) is at least $30,000 -- should definitely factor into your compensation negotiations.
If you're employed, then you and your employer have compulsory contributions into all three of your CPF accounts (Ordinary, Special, and MediSave). If you're self-employed, you're only required to contribute into MediSave, and you don't have that 17% from an employer. You can contribute to all three accounts as if you were employed (and with you carrying the "employer's share" that you aren't getting), and then you get tax relief when you do that.
Basically, uplift your salary demands to account for that missing 17%, maximum S$17,340 per year (the highest figure an employer would pay, if you hit those salary and variable pay levels I described). Then it's up to you whether you want to make "all three" or just MediSave contributions (or somewhere in between), but I'd lean toward the former.
There are also potential personal liability considerations, so you'll want to give that some thought at least.