Hey @Nick Gallon Martin, I recommend speaking to a Tax Planner/CPA, @Jeff Nash would be a great resource for you.

I looked into this as well since I'm getting terribly bent over on my w-2 taxes. 

Now I raised claim Immideatly.

If you live in the home for 2 out of the past 5 years and move out of state you may be exempt from the tax.  

I'm in the market for entity config and tax planning/prep.

Simply gifting him half the property now wouldn’t immediately allow him to claim the exclusion without fulfilling this residency requirement, I don't believe.One thought would be to use a HELOC to pull just enough equity out of the current home and use it to buy a smaller home, or at least the down payment.

At a 7% annual return, this could grow to $908K after 10 years, providing immediate liquidity and diversification.Alternatively, holding the property could yield $825K net equity after taxes in 10 years, assuming a $900K sale, with the potential to defer taxes via a 1031 exchange if reinvested into another property.

I'm talking about tax season! 

The absolute best way to avoid taxes is not earn income.  

This is also tax deductible.