Now the directionless ride might be a lot of fun and you may make enough money along the way to be happy and pay the bills. 

As @Scott E. said, the RE market is NOT a guarantee of easy money any more than the Stock Market is....And instead of having a bunch of small-er stocks, you will have your money in large chunks tied up in different properties.But I prefer the RE market anyway, it's just not an easy ride......

There's close proximity to major businesses (particularly in finance/legal), Trolly Sq is a short car ride away for the younger crowd, lots of restaurants on Market, and around that.

As you got the loan in Dec 2021 you probably have an amazing interest rate, ride it out for the next 4 years, and then look at interest rates and value.  

Not sure about triple coats of primer, sounds like this guy might want to take you on a ride for unneeded expenses.

If you are stable enough to ride out a few months at current rent, that makes for a much easier transition.Taking the hit for 3 months to give her room to plan could save you 10X that much... if the agitated tenant decides to stop paying all together.

I am taking a ride on the Golden Hamster Wheel. 

When you invest in 2-4 unit real estate you have a fixed mortgage and can ride out the market ups and downs, you can also just invest in SPY take a 4% withdrawal and average 8% while holding through downturns.

I lived in Indianapolis for about 7 years now and ride my bike all over the place. 

We’ve had a lot of storms in the last year so I’m guessing you have some wind and hail damage.