[ndriscoll]

I suppose it depends on how spectacular your buying is (a common criticism of sales tax is that rich people don't buy much, relatively), but wouldn't you only need enough tax lots that are close to current market value? If you've been accumulating, you've probably got a blend of tax lots from "nearly 0 gain" to "nearly all gain". You're also going to be receiving some dividends or have some other income sources that you presumably re-invest to create recent tax lots. The only case where that wouldn't happen is if you got lucky on a concentrated bet you made. If you inherited your wealth, you got your step-up, so you're faced on day one with "okay I have tons of assets with cost-basis at market value, how do I do rich person tricks?" Is that group not a good fit for buy-borrow-die, and it only works for founders/early investors of companies that blew up?

Taking on loans also means you're adjusting how leveraged you are, so I feel like there's a missing risk analysis component here. Otherwise of course I'd just take out as many loans as I could right now to get that sweet 10% expected growth at only 6% interest or whatever. So I can't borrow to avoid the tax man because I already borrowed as much as people are willing to give me.