As I think about this, I see that international law and policy has a hard time keeping up with the effects of global technology with respect to remote working.
My guess is that if you were to create a sole proprietorship, it would not change MoM's response with respect to the need for a work permit, for the situation of a foreign employer, etc, has not changed.
Your IRAS reporting would change in that you would have to file a SP return as part of your personal return.
However, there is yet another wrinkle for you to consider. As you have previously noted, the Business Registration act provides for no registration at all if:
4.—(1) The following persons are not required to be registered when carrying on business in Singapore:
(a)
any individual proprietor carrying on business under only the individual proprietor’s full name;
My view (and I am not a lawyer) is that if you believe that you would have the necessary entity in kind without a registration, then you can always claim to be working for a Singapore entity registered in accordance with Singapore law and let it go at that.
Or, go ahead and register a named SP. Again, my view is that if the Singapore authorities were to actually look into the setup, you'd be in good shape. You are not conducting business in Singapore, and given that the intent of the SP is only to avoid double taxation, you're clean.
Lastly, contact IRAS. Explain the situation. They will provide a ruling that may work in your favor without the need to have a legal entity in Singapore.