I owe around $1000. in Federal Taxes. I want to put some in an HSA or investment account to off set this amount. How do I know how much I should deposit?

Do you have a High Deductible Health Plan?

For 2020, if you have an HDHP, you can contribute up to $3,550 for self-only coverage and up to $7,100 for family coverage into an HSA. HSA funds roll over year to year if you don't spend them. An HSA may earn interest or other earnings, which are not taxable. 

if you're in the 20% bracket you have to put in five times that amount.