With out a hospitality license and insurance there is a lot of risk and liability involved when selling to strangers, so definitely do your research.

I love how everyone just jumps in and inputs what they think is best for a stranger they've never met. 

I also recommend that you don't be a stranger to the management/maintenance team either -- regular contact & inspection and keeping tabs is always a good idea as things can go downhill fast. 

I personally do not trust strangers and assume something may be fishy if they need to move in less than a month.3) living within an a hours drive is easy to access and should be no need to hire a PM.

You are lending money to a stranger that you do not know their credit history (why can he not get a normal loan?? 

Being from the other side of new York and already having been in the area for five years, you should be no stranger to the snow. 

A simple email or phone call to a total stranger and the job is done.

@Jason Coleman please don’t rely on the “advice” given on the Internet by strangers.

It is very unlikely that two strangers will want to share a room. 

Now for a corner-case scenario: Your property manager rents your IRA home to a stranger who subsequently meets and marries your daughter.