I’d pay off the rental first

Then when you sell it you pay off your house with the proceeds and bam both houses are paid off!
But if you payoff your house first, you have a paid for house, but you still have the rental to pay on while your dad lives there.
Logically, they both payoff the same, but mentally paying off the rental is like paying off a debt. When that is paid for and you sell it, you get a big fat check! Then you take that money and pay off the mortgage on your house. It feels like found or made money!
Notice the word feels, it feels different than just selling the rental and giving the money to the bank to payoff the mortgage on the rental.
Its all about the excitement of being gazelle and paying of the rental and then reaping the benefits by being able to use that money to payoff your mortgage.

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!!!!