I am self-employed and my income fluctuates each year. I always pay quarterly estimated taxes each year, and I always file an extension every year, giving me more time to contribute to my individual 401k, which affects my final tax due amount.
This year in January 2023 I sold my rental property. I am not eligible for the capital gain exclusion so I will owe a large one-time capital gains tax on this sale.
My question is this: when do I have to pay (estimated) capital gains tax on this sale? Do I have to pay it now (April 2023) in order to avoid penalties? Or would I be safe paying estimated taxes equal to 100% of my tax bill from 2022? (I don't know my 2022 tax bill yet as I have an extension to October 2023 to file, so this would also be an estimate).
The amount is sizable enough that if I can wait to pay the capital gains tax until the 2023 tax deadline without penalty, it would be worth it.
Thanks for any advice
