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Should I fully fund my SEP IRA and HSA which lowers my tax, but uses up 1/2 my cash or do I just pay the tax (I am assuming I will incur a penalty as well)?

My advice is highly influenced by my current cash conservation mode coupled with years of trying to collect taxes from the self-employed. I'd hang on to the cash as long as I could, until you have a sure source of income flow.

I'm not sure of the last date that you can contribute to your HSA, but if it's April 15 I'd make that contribution. I know that you can delay SEP contributions until October.

Take a look at annualized income in Pub 505. It may save you something on the ES penalty.

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