[alistairSH]

But surely, you're on the cusp of itemizing. Or have dramatically changing circumstances year to year. Otherwise, you're just wasting time.

FWIW, we are in the "on the cusp" boat. Another year or two and our mortgage interest vs principle equation will put us in the standard deduction range. And short of massive changes to either tax law or our income, we'll remain there.

[elicash]

Last year I had lots of investments that I hadn’t previously. This year I sold a home. Next year, I’m planning to get married. The year after that, a new home?

Maybe these are “drastic” changes but they aren’t unusual across the population. Not planning on kids, so that means I’ll have fewer changes than most. But the person I plan to marry has significant changes to income based on commission so I’ll probably be doing taxes this way for a long time!