How do you continue to improve your analytical skills while also not redirecting precious time from your criteria window?

My decision comes from wanting to improve scale, cashflow, and ROI. 

My question is how much room is there for improvement in those rental numbers? 

This way you don’t have to worry about improvement.

Renting it out for enough time cover costs and allow me to write off improvements I would want some day and the trips to work on it. 

Improving myself every day!

And what your goals are.I.e. the longer you hold, the better your multiple but typically the lower your IRR.And of course, will the "repairs" improve the value/rent potential of the property, or is it maintenance like a roof, that costs a lot but has marginal effect on value.

I would simply ask for occupancy history, financials on the property and a list of improvements. 

“Rent strikes are usually used for two things: to get landlords to lower the rent or to get landlords to improve conditions,” said Peter Dreier, professor of politics and public policy at Occidental College.

I have been seriously thinking about improving my parents rental property (which I live in) and adding a 1/1 in the back or 2/1 if possible.