I'm thinking that it may be best as my own family retreat offset with the occasional VRBO and/or hunting lease on the property.  

This is occasionally not difficult at all these days.

There will be more wear and tear and occasional damages but you can usually recover them from guests and the extra money you make will more than cover it.

If you do this make sure your long term tenant is laid back and will be ok with people coming and going and occasional load noise. 

Historically over the last 10 years, while there have been occasional dips or losses, both stocks and real estate have increased in value substantially over the long term.When directly comparing the purchase of 1 stock of S&P versus 1 average Massachusetts multi-family, the ROI of the stocks is nearly double that of the real estate.

She occasionally hired a contractor (such as handyman or plumber) to perform tasks she could not complete herself. 

I occasionally shop estate sales for this purpose.

‘Just’ the occasional lease/ property abandonment issue. 

I have a couple agents that help me with comps or submitting offers on REOs occasionally, but that's about it.

I find I can do well enough in real estate with old-fashioned on-market deals, or the occasional pocket listing from an agent, without having to deal with the properties or places that are experiencing turbulent personal problems.