[hhw]

This would count as capital gains, so (33% federal + 14.7% provincial) / 2 would be closer to 23.85%.

That's not counting the portions that fall under lower tax rates, or the lifetime capital gains exemption of $750,000.

If he did structure it under a holding company, he could better spread out the payments over a number of years so that more of it could fall under lower tax rates.