A few things

After too many months of being broke, poor and under-employed, we’re finally in a happy spot, income-wise. We should pay the car off in October.
My question for the visitors: I have a rental that my father is renting from me.
I’m not sure what my next move should be. I owe about $27k on it and $66k on my residence. When my dad no longer needs to live there, I want to sell the rental. It’s worth $60-65k.
I could have the rental paid off in a little over a year (after the car is paid off) then start paying extra on our mortgage. Or pay our house off first then the rental, because I might sell the rental within that time?
My dad will be living there as long as he is able to, as far as we are concerned, but we don’t want to play landlord after him.
So should which house should we concentrate on paying down? When I run the numbers, it doesn’t make much of a difference on paper. Either way, WE’RE DEBT FREE in 5 years!!!!