Estonia's E-Residency Program Is Growing Faster Than Predicted

First, it's expensive - you should count a good S$5k SGD/year if you go through an established player (e.g. Hawksford, who you are quoting), maybe a bit less otherwise. This ad infinitum, as you need a local director to keep the company open. And unlike in Hong Kong not so long ago, it has to be a real director - someone who theoretically can open bank accounts and hire people - so you're taking that risk too (the director will, conversely, be taking the risk that you might be a scammer or other criminal whose acts he'll have to answer for in court).

Then you have to put in S$50k in capital in order to be able to apply for a visa (EP) for yourself, should you want permission to work in Singapore (if not, you'll get taxed at home when repatriating profits); this visa will require, today, at least S$4-5k/month in "salary" (which will be taxed).

This also assumes that the Ministry of Manpower doesn't suddenly catch upon this very convenient way of getting yourself what is effectively an investor visa at a fraction of the investor visa cost (which they did two years ago with the EntrePass, which is today utterly useless for most foreign founders due to its requirement to have funding from a short list of approved VCs). Guessing what MoM wants and is going to do seems to be a bit of Kremlinology which HR directors love talking about as their special value add, but it is a bit opaque and the rules change with time, elections and special circumstances (like the famed riots last year, or the Ferrari and taxi incident).

The "plan" should you want to take advantage of Singapore's otherwise fantastic conditions for running a business is to get PR, which takes up to 3 years employed locally (depending on salary - someone on a high salary and from a "desirable" country might get it in 6 months). Singapore is fantastic... for local founders. Or if you're willing to pay.

The days where you could be in business for USD 1,500 and a flight to Hong Kong appear to be, unfortunately, over. I'd love to be proven wrong...

Despite there being double-taxation treaties with several countries, Estonia taxes the company paying dividends, and not the individual receiving them, so you may not be in a double-taxation situation. But I am not a lawyer or an accountant; it is better to consult with one.

The general principle I stated is the one employed in the U.S. Generally, when one receives money there are tax implications. There are some exceptions to this principle but this is the general idea. The different ways of receiving money have different tax rates and this causes a skewing of how "income" is begotten in the U.S. by the very wealthy. They prefer getting money via capital gains since the tax is less that route.

I don't think one can reasonably argue that not taxing one form of income would lead to people preferring to get income via that tax free route. The objection I had to your original post is that the U.S. tax principle is bad. It is reasonable to tax all income streams. I don't know the optimal for each stream but given that taxes in the U.S. are low relative to the past 70 years suggests the rates aren't burdensome.

The issue is not taxing personal income, the issue is taxing corporations. A nearly ideal situation would be to eliminate all corporate taxes and tax individuals at a fixed rate when corporate wealth is transferred to shareholders. The only better situation would be eliminating all income taxes and replacing them with consumption taxes.

Unfortunately, this is a political non-starter - it would eliminate the ability of politicians to pretend they aren't indirectly taxing people when corporate taxes are raised.