Renting out rooms isn’t a feasible option for me as we have dogs who are not so stranger friendly so we’re looking for a property with a separate casita/guest house to rent out.

You can not just hire strangers , pay contractors and keep your fingers crossed all will go well.

It feels a tad rude to ask a stranger such personal questions on a public forum though.

The tenants all know each other and no stranger can walk on the property, without someone saying something.

Don't base your decisions off the advice of anonymous strangers on the internet that know nothing of the situation.

Why are you second-guessing him and asking a bunch of strangers on the internet?

You could also buy in MA and charge a stranger market rent, however you really don't know where you'll live when/ if you come back, so if it were me I'd go for more pure investment properties.

We aren't complete strangers to the market: I did an internship around Cincinnati and northern KY (Fort Thomas mainly) for a summer a few years ago and she lived in East Walnut Hills for 6 yrs until moving to DC 2 yrs ago so she knows the area pretty well.

The neighbor informed them that he was as astounded as they were when he saw the stranger  suddenly appear a couple of weeks before (beginning of August) with a van and start quickly unloading his stuff.

Question: Has anyone ever purchased property with a near stranger?