I was thinking I'd provide property management for small tasks that are difficult for elderly, provide a weekly cleaning service and lawn care, but beyond that, they'd be on there own to maintain the home. 

If I am physically there, I like to do the repairs myself, but I understand that can be a daunting task if you aren't handy.

Whether you have one rental property or a portfolio of properties, property management can be a time-consuming and challenging task.

But now it's sat vacant for a month (that did allow us to touch up the exterior and address a few items that needed enhancing, so looking at the positives, that's gotten done).

Unless it’s some arduous task or costs 100s of dollars I’m not sure why you wouldn’t.  

And, never forget that bidding a job is a time/money consuming task for most contractors.

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- Run financial reportsIf you do a task with one system, do the exact same task on all systems so you can see which one is more efficient, easy to use, etc.

You mentioned contractors so maybe you should target a home that needs light cosmetic work to enhance its value.

I'm at the point now that the non urgent tasks seem to get pushed to the the back burner.