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Additionally, I think you missed the point of my objection "You have to put in work". If you successfully spend $X on reducing akrasia, then your work for the rest of your life will be more efficient; great. But you still have to work for the rest of your life. If you invest $X in income-generating capital, then you have income for the rest of your life without lifting a finger.
Yes, if your goal is specifically to do as little work as possible and don't care about either your standard of living or what your ultimate net worth is (as long as it's enough to stop working), then you maybe should invest in as much income generating capital as possible, depending on your exact circumstances. If you are interested in increasing your income or increasing your standard of living (or have a number of other goals, such as making a greater impact on things you value, having more satisfaction from achieving more, etc.), then it is quite conceivable that self-investment would beat traditional investment in fairly short order. Let me make up some numbers that I think are reasonably plausible: Let's say you make $20,000 per year and have decided to invest half of it somehow, and that you can double your yearly income if you spent $10,000 on the problem, and that you could get a 10% return on traditional investments. [Justification: $20,000 is a very low salary in developed countries, and $40,000 is still a fairly low salary, so it's not unlikely that a relatively small improvement could take you from one to the other.]
If you then invested in yourself for one year before you started saving and investing traditionally, after ten years you would have saved about $185,000 vs. about $320,000 from the one year of self-investment. After 40 years it would be a bit less than $5 million vs. a bit less than $9 million. If you could keep getting returns on self investment after the first year, the difference would be more pronounced. If you got less than 10% return on traditional investment, the difference would be more likely to be greater.
There are a lot of people who make minimum wage, and some people who make thousands of times minimum wage. If it's possible to teach yourself the skills that the people who make thousands of times minimum wage have by spending money on it, it's likely to be worth much more than a standard 5% or 10% per year, since the income that some people make would take you many decades or centuries of saving and investing just to equal what they earn now. If you can increase your income by much more than the standard return rate of 5% or 10% per year, then compounded interest will quickly dwarf what you could make by investing in the stock market. So I think it hinges on the question of how likely it is that you can increase your earning potential faster than standard investment returns. It seems to me likely that this is possible, given some people have achieved it, and that most skills are learnable.
A separate point is that traditional capital is perhaps more likely to survive the Singularity without being drastically reduced in value than is human capital, on the grounds that atoms are still going to be in finite supply while akrasia-reducing brainware patches will be downloadable from the Internet.
This is difficult to estimate, but I tend to think that the Singularity is probably far enough off that significant self-investment in things that are helpful now is still likely to pay off.
I agree that this is a significantly different proposal than the original idea. It's a combination of the original idea with another idea in a munchkin-like fashion with a different result, but one that is potentially better/more powerful/has higher XP (though it's not guaranteed, of course). I wouldn't call your points problems though, just differences.
By the way, there are ways of getting yourself to put in the necessary work (i.e., overcoming akrasia), and this community is great at coming up with a lot of them. Do you think that if you had $10,000 (to throw out a number) to spend on improving yourself and you decided that akrasia was your weakest link, you could come up with some ideas/systems which would make a significant difference? Is that likely to be worth $10,000?
Likewise, small amounts of alcohol (1 or at most 2 glasses) has been shown to increase creativity. As with coffee you will have to check your own personal reaction to it.
Combine this with the idea that the most worthwhile investment by far is investing in yourself. Take whatever percentage of your income and use that to help you learn skills that will increase your income. (This includes not just technical skills, but self-marketing skills, self-confidence, anything. You will probably have more and more ideas the further you progress.) Most likely, you will have a much greater return than if you simply invested the same money in more traditional investments like the stock market.