I recommend reading books, listening to podcasts, and making it a daily routine to read several posts per day on this forum.

The biggest issues we faced was equipment breakdown as customers routinely abuse the equipment  the most common repair ws due to over stuffing the washers and using the washers to dye items.

It has become routinely challenging to get appliances ordered, delivered and installed in a timely manner due to supply chain and labor shortages.

I love your book list, you could add the One Thing from Gary Keller, it changed my morning routine and helped move our company forward.

the last part of that sentence is where the issue lies. you have to get into a habit and routine of putting in the hours for yourself. you have to find the motivation either internally or externally via somebody else keeping you accountable at the end of the day the question you have to ask is "How bad do you want it"? 

Honestly, he had them on his forehead, his eyebrows, his ears, his chin, his neck and EVERY body part I was able to view in someone wearing a short sleeve shirt and shorts. 

Do they routinely change out cast iron plumbing, aluminum wiring, test for lead-based paint?

To be honest, 30+ minutes on a dirty CTA each way is not something I’m willing to do, I work 70-80h a week (that’s my “little sacrifice” already) so it is important to keep my daily routine optimized, and walking to work from River North/West Loop is not negotiable.That might as well mean that it’s better for me to keep renting rather than “investing” in an overpriced condo. 

Rents are high, we have many clients getting $1300/month for routine 3/1 houses.

Routine maintenance doesn't seem difficult.