For the $525K property, with the low mortgage rate(you will probably never get a such low rate), it might make sense to hold onto it for now, especially if you can still sell it as a primary residence within the next three years and avoid capital gains taxes.

@Kris TohovitisI wouldn't recommend using your cash to pay off the mortgage on your primary residence since you can likely get a better return on that money by investing it.What's your buying criteria for the multi-family property?

I'm not sure that the property being perfect for your investment criteria makes it unique enough to warrant a judge forcing the sale, especially considering that it was not listed for sale to begin with and that you're going to be using it for an investment property not a primary residence.

Hence the lot on which the house resided was taxed at a 45% discount based on actual value, while the tennis lot was taxed at about 4 times what it should have been by value. 

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The last thing I would do is aggressively pay off my personal residence, especially if you have a low % mortgage.

When I return to the country after my Au Pair contract ends, I hope to live in the property as my primary residence and house-hack as well.I understand that investing remotely makes things more challenging, but I am also ready to be uncomfortable and challenge myself in this journey as I know it is 100% possible.

I just completed an exchange of a single family residence in Scottsdale to a single family residence in Durango, Colorado. 

@Bobby Short Depending on the equity you have on your primary residence you might be able to find a lender to finance the property in CR with your primary residence as collateral.

Investment Info:Single-family residence buy & hold investment.