@Michael Baum I didn’t think about preparing for replacing the furniture.

Try to come to a settlement of replacement value with the tenant.

If you go that route then a consideration would be selling to them but they give you a floating closing date so you can have more time to search for your replacement property. 

"Most" gets a little weird though - for example, in Michigan, you can strip and re-shingle a roof without a permit, but you have to pull a permit if you replace even a single square foot of the sheathing under your new roof.

VTSAX doesn't have a furnace to replace, and it is nice to be completely liquid in a good portion of your investments.

The driveway near the garage and inside the garage has large cracks from tree roots, but probably has a few more years life in it.My question is whether, in the next year or 2, I should replace the drive and garage? 

Refinance means you're replacing an existing mortgage -- that isn't the scenario you're describing.

It's not AI replacing people per se.

This debate is like arguing if it's better to buy a car with an engine, or tires. 

There will be other large ticket issues that pop up as well as big things that will eventually need replaced like the roof, furnace, plumbing issues, etc.If you have enough properties for enough time the below or worse will eventually happen and repeat itself.