[leetcrew]

I don't think it makes sense to tax the appreciation of an asset over twenty years as if it were a single year of outsized income. if you want to treat it similarly to income, you should divide the realized gain by the number of years the asset was held and assess taxes as if the person made that quotient in income for each of those years (under the rules/brackets for each year, possibly with some adjustments for inflation). this would make it harder for average joe to estimate his tax liability when he sells, but it prevents the tax optimization you mentioned and is (imo) pretty fair.