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That is an excellent writeup, but misses the key argument:
is really just a fancy way of differentiating "realized" income (where an asset was sold for more than you paid to buy it, and you have the profit in hand) vs. Unrealized Income (where an asset is valued at more than what you paid to buy it, but you haven't sold it yet). It is more of a burden to tax unrealized income, because some unrealized assets aren't able to be sold easily and applying a tax to those may force those assets to be sold early if the tax is high enough.
So while it creates loopholes where the wealthy can structure their businesses so they take a very low personal income while financing much of their lifestyle from their unrealized assets, there is also an element of fairness in it: imagine the shitshow if you had to pay extra every year if you owned a house outright but the property values kept going up?
The answer is in the plain text of the 16th amendment, though:
Where it gives the Congress power to collect taxes on all incomes, full stop, without regard to whether they are realized or not. Congress does tax unrealized income, after all, such as on estates, they just do it with a large amount of restraint because they know that it's not always appropriate.
And while normally we can count on this Conservative court to vote in favor of the plain text in the Constitution, I am not so sure on this one. Perhaps the writers of the amendment should have had the forethought to throw a "shall not be infringed" in there, since those are the only words some Conservatives know in the Constitution.
"imagine the shitshow if you had to pay extra every year if you owned a house outright but the property values kept going up"
Like property taxes, then. ;-)
Realistically, I understand the issue. If I had to pay taxes on the increase in price on my house (say from a $300k valuation three years ago to a $500k valuation after the market bubble), I'd be fucked to find 15% of that overnight. Of course, if they allowed that to be offset by the primary residence exemption, it would be a zero cost. Without that, it would still be a non-issue for 95% or more of US taxpayers because most people simply don't own an illiquid asset that increases in capital value (much less an international one), and if you exclude secondary real estate that non-issue number probably increases to more then 99.9%.
My other big question: What about times when the asset doesn’t pay off? Does the US government cut me a check or did I just get taxed on money that never existed in the first place?
When the asset doesn't pay off you get to write that off on your taxes.
So when something like 2008 rolls around, the US Government just gets 1/8th its income at a time it really needs to pay out?
YES! And this is the problem with profit based taxes. You should be taxes on what you have (property taxes) and what you receive (gross receipt taxes). The ebb and flow of commerce does vary, but the overall work and wealth is more stable. It also makes taxes harder to dodge as there are no deductions for expenses or other items. My local business tax is this way - I pay a couple percent in fixed assets tax, plus a (I think it's less than a) percent on my gross receipts - take what your paid, multiply it by 0.012, send that amount in. Simple, effective, and relatively consistent. It also, in a very simple way, reflects that government services are not a bonus the town gets when you make a profit but a cost of doing business. My power company charges me whether I make a profit or not, as does my web service, my copier maintenance plan, etc.
That puts it pretty simply, but yes. And at least in 2008 it was mostly loans instead of hand outs so it got paid back.