Fund roth IRA, pay my taxes or keep saving.

[Djuan Snowden]

Hello all,

My question is not 100% related to buying or selling a piece of real estate but it does relate to financing and getting things in order to purchase my first investment property so I hope it can still get some answers.

So, I am an 1099 independent contractor. Currently I have a large balance due in taxes for some previous years (2017, 2018) that I am making $300 payments on. I have the money to pay it off in my savings but I dont want to deplete my savings an Im considering using that large amount to help purchase my first property house-hack style.

I now have a new balance for tax year 2020 (around $5,000). I am waiting on an invoice to be paid out for that same amount. At first, I was going keep paying my taxes monthly, adding my 2020 balance to my 2017 and 2018 balance, and use that invoice to fund my Roth IRA for 2020 before the April 15th deadline. So, should I fund my IRA for 2020 ($4,320 left to contribute), pay my tax bill for 2020 or keep saving for a property? I dont have to pay my taxes by April 15th as I already have a payment plan arranged and the interest on the payment plan is bearable. The IRA on the other hand must be paid in full by April 15th in order to maximize the amount allowed per year and I believe I can borrow from it later in regards to a investment purchase. Or should I keep saving and add that to what I have saved so far for a down payment on my first property?