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. 

Tenant shall not make any repairs alterations or improvements in or about the Premises including painting wallpapering adding or changing locks installing antenna or satellite dishes placing signs displays or exhibits or using screws, fastening devices.I wouldn't have minded the swing so much if the tenant hadn't already demonstrated in the past that he is quite savvy with the lease when I had requested that he provide receipts for maintenance items that the lease specified that the renter is required to take care of. 

I occasionally shop estate sales for this purpose.

But if I were to create a list of random things like, please clean all dishes upon move out and place in drying rack, place dirty linens in XYZ location, take trash out upon leaving, etc. does that really go in a lease??

‘Just’ the occasional lease/ property abandonment issue. 

You will replace chairs with broken legs, towels that are stained/missing, dishes that break or wind up in the rental car, ping pong tables that get jumped on..but you get paid every time they check-in, not like a LTR where the tenant can withhold payment if they feel you should come fix the toilet they clogged up.Hope this helps.

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.