then start selling the ones that have upcoming major repairs in the next 5-10 years or the ones that are a biggest pain to deal with/make the least amount of money from rent.

I would say it depends on if the property is a pain and what your long term goals are.

And that is VERY painful for me to say because I LOVE HD, and go there for almost all of our rehab projects.However, if you are leaning toward the White cabinets, I would suggest that you compare to Lowes. 

The biggest pain points like others mentioned is the Pre-Payment Penalty, Lender protections, and undisclosed fees. 

Until they are confronted with something life changing, like losing a job, and then the pain gets too great and they need and want to change.Congrats on your journey to financial independence!

Right now, Stayfi has been beyond a pain!!

You can do the same, find the pain point and solve it.

I have lost one in the past and it was a total pain in the butt when the tenant moved out...

Does anyone have any pain points / challenges that they'd love to share?

You get better with time, you learn from painful mistakes more than from your successes, but that's when you become like Jonathan and tell other people it wasn't that easy.