In this situation you're essentially trying to increase your adjusted basis in the property so that you'd pay less taxes on capital gains and alternative minimum tax.
Honestly, I can't think of an answer that would solve this problem off the top of my head right away in the 3mins afters reading your question and here's why:
Regardless of how you transfer these assets, they're going to be transferred based upon your current tax basis and your still going to be paying cap gains every sale.
Ex.
You sell for. $100
Basis is for. $50
gain is for. $50
Later through a series of transfers, you regain your shares at the FMV. New basis is. $100 but you already paid the cap gains tax at every junction so the whole series of transactions was pointless.
But, I'm sure there has to be a way to get around it and I just haven't thought of it yet lol. Give me a few hours and I might be able to string together a plan. I'm going to think this over and see if there's a way over the day.
If it's a ROBS, and you invest using already-taxed Roth IRA/401k funds as a rollover into a Roth 401k, you actually don't care about the basis. You just want to characterize it as capital appreciation on an asset acquired in the Roth.
My understanding is ROBS, aside from being hated by the IRS if they step even slightly out of compliance with 401k regulations, are basically close to magic. $50k to set it up, invest $50k in a company to give it $50k capitalization, and sell the company later for $10b; zero tax owed.
With the SBJA2010, you have a similar deal; as long as the capital gain is due to the sale of a qualifying asset, you owe no capital gains, and it doesn't fuck you for AMT either.
I'm going to have to say that I'm not familiar with ROBs, since I never came across it. But, its definitely peaked my interest. From the preliminary reading I've done on it, it's a very aggressive tax planning vehicle and highly despised by the IRS. Which means it probably is as amazing as you say it is.
Allow me some time to read up on the case law in regards to this topic and I'll email you directly if you don't mind. This is something that would definitely be more than a 30 second answer and I'd definitely be interest in discussing it merits and shortcomings with you. Thank you for bringing it to my attention! No matter how many years I deal with taxes there's definitely going to be a lot that I need to learn lol.
And or thoughts on same using small business jobs act of 2010.
Goal is capital gains and amt minimization for scenarios from 10mm exit at 18mo to ipo and billions in 10 years, just to cover possibilities.
The irony is I'd probably donate 90 percent after a certain amount.