TomD8
Level 15

Deductions & credits

I think the exceptions to "generally" refer to the various situations described on pages 52-53 of Pub. 505 - such as high-income taxpayers, farmers and fishermen, timely estimated payments, etc.  There is no rule specific to sale of a second home or LT capital gain.
**Answers are correct to the best of my ability but do not constitute tax or legal advice.