Selling investments to cover VA loan assumption

[Nicholas Curcuru]

I just moved back to the USA and want to buy a property. The property will be my personal residence (VA loan requirements) but it will be a house hack as well. I am planning on getting 2 roommates to cover almost, if not all PITI. Interest rates are still high for me but I can use the VA loan assumption process to get the seller's existing, and likely very low interest rate of 3% or less. The largest problem with this route is I need to pay the seller's equity and appreciation amount over the existing loan. Given the amount of market appreciation, this can be $100k or more.

I have over 100K of non-retirement investments in mutual funds in a brokerage account that I wish to sell to pay for this 'down payment' on the loan assumption. The problem is I want to avoid getting murdered by capital gains taxes. Right now, for 2022 I am at a loss.

I am looking for insight of how to sell smartly between now and the end of the year as well as more in first few days of January to maximize my VA loan assumption and tax situation.