Counted my 180 days from the wrong date, so the deferral evaporated
The gain wasn't mine directly, it came through a K-1 from a partnership that sold an industrial building in June. My share of the gain was $237k. I'd already picked a fund, had the subscription docs sitting there, and I was pleased with myself for being early.
Then my CPA asked which date I was counting from. I'd been counting 180 days from the closing in June. For a gain that flows through a partnership there are different possible starting points depending on whether the partnership itself elects to defer or the partner does, and one of the choices runs from the last day of the partnership's tax year rather than the sale date. I had it backwards. I thought I had until December and I actually had a different window, and by the time we sorted out which one applied and got the partnership's paperwork in order, I'd missed the one I needed.
So I paid the tax. Federal plus state, call it $71k that I'd budgeted as deferred. The fund was fine about it, released me from the subscription with no penalty, and I felt like an idiot for about a month.
What it actually cost beyond the tax: I'd sized my next purchase assuming that $71k would still be working for me. Had to shrink it.
What I'd do differently. The moment I knew a gain was coming through an entity I don't control, I'd get the CPA and the partnership's accountant on the same call before I looked at a single fund. Get the eligible start date in writing, from the person who prepares the return, before you start shopping. The fund selection was the easy part and I spent all my energy there.