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First I would say it's unlikely you can be a "shady landlady" because a), you're asking the question, and b) having talked to you here I don't think it's in your character. 

I attribute that to because when it's all on the line, there is no way that I will let myself fail.

Specifying certain material attributes and having liquidated damages provisions to keep contractors on schedule are good ideas. 

If you go that route, I'd recommend someone who has a track record, shows good character, and has a large community.

While I know it will be run safely and professionally by the wife, clearly there are concerns over liability, wear and tear, potential neighbor issues, etc...Only because I know their character, I would like to make this work somehow.

Plus too many STRs does change the character of a neighborhood. 

you provide those three attributes and tenants will stay.

It's definitely a more clean/contemporary look, so make sure if your using it, it fits the character of the house.

My 1st flip was a cute little brick ranch that had lots of character left in it and it was fun restoring it.