The back has one and a half apartment that is occupied.

If it takes an extra 30 days to find a tenant at $1000, it will take up to a year and a half of tenancy to make up the difference.  

The small investor, with SFRs or small multi family, and within 50 miles range.

If rents are in a normal distribution (bell curve) like they should be expected to be then half of the units will be below the average and the other half will be above, you need more information before making a decision. 

Over the years I was really uninformed about it I thought you just collected all the rent and paid about half of what you make a month for all the expenses.

So it's possibly better in the long run if you pay it off, save the non-deductible interest on any car loan, then keep it for 10-20 years and/or 200,000 - 400,00 miles. 

The headache of dealing with contractors from 3,000 miles away makes me shiver.

ALSO- Hurricane Michael hit about 40 miles away with damage within 10 miles of this location.

And I'm assuming you'll have miles of red tape with local municipalities on this as well.

I'm about half way through them and I feel like I have a pretty solid grasp on how things work.