@Bettina F. I was smiling inside while I read your post above. Especially the lines about starting in your 60's and "We have learned that the skill set required is actually fairly limited. You end up doing the same tasks again and again."
This is exactly how I started. I knew that I couldn't afford to be in the Landlord business if I hired everything out, but I quickly learned that I could learn to do just about anything, and after I learned these skill myself, it would become very easy to estimate labor/material costs when scaling up and dealing with sub contractors.
@Joshua Feit , in my opinion, this is a people/relationship business. $1,500 to repaint the interior of one house may be a simple time management decision. But what about when you have three houses? Five houses?
Wouldn't it be more cost effective, "time management wise", to do the "work" necessary to cultivate one or two "small guy" painters who can handle those interior repaints for you? And maybe that "small guy" painter will turn out to be a great guy who will refer you to a "small guy" tile layer? And so one relationship leads to another...
If you do let the property management company handle the painting, please do us all the favor of stopping by to interview the painters themselves. Are they driving company trucks? Are they licensed and insured? OR is the property management company "handling the job internally"? And if this is the case, can the property management company show you that these personnel are legitimate property management company W2 employees working within the scope of their workers comp insurance job descriptions. : )
One last thing that I will disagree with everyone else on, and that is the use of Flat Paint. I love flat paint in rentals, other than bathrooms and kitchens of course. I would rather spend the "clean up" time simply painting over dirty walls. Plus you get that "freshly painted" smell even if you only did a few spots on a few different walls. New tenants love that freshly painted smell and flat paint will always match perfectly on touch ups.
DL