[geoelectric]

In the US, at least, the problem is that you realize the gain in a single tax year, but there's a limit on capital loss writeoffs so you have to spread that over a multi-year rollover. It doesn't balance.

Also, we have AMT (alternative minimum tax) which gets triggered by this kind of scenario--exercise and hold--and really ends up screwing you due to outdated but not updated calculations that assume anyone making over 150k or so is "rich".