Thank you to everyone who took the time to respond, I appreciate it greatly!!

I would agree that there is much to be said for simply paying the tax now, rather than seeking shorter term deferments that have their own drawbacks and future obligations. We have discussed the advisability of future IRA Conversions in the years after he retires. IF in fact, there are no other changes to the tax code, of course. And, yes, he exercised AND Sold this year, and will for the next three years. I do wish he had been my client many years ago because he is definitely not diversified with industry or account type, but he will be, before we are done. It just might take a few years to get there. 😉 

Again, thank you for being other 'sets of eyes' as they say. I find that sometimes I get too deep into a case and can potentially miss the obvious, lol. 

Oh, and I will check out the Qualified Opportunity Funds, although, I think that might be a long shot at this point, but good information to brush up on. 

Cheers, Dawn