I agree with Adam.

Being from Chicago, I'd tend to agree with you @Craig Jones those areas of Wisconson and & Michigan are driveable from a lot of those metro areas you mentioned, but I think the toughest part of any northern short term rental is the seasonaility. 

And that includes wraps .. wraps done right protect the seller and you.. investigate that avenue.Have to agree with you Jay….good advice as usual  

I agree with Laura, if this is a long term rental it would be hard to convince the tenants that they have cameras on the property that the owner controls even with all the stuff that you mentioned (does not turn, only for surveillance for crimes etc.). 

Agree Jay Parsons is a thumbs up to follow !

My PM already charged me for their diagnostic visit (a month prior), which we seem to agree is shady.

Its hard to find a perfect spot anywhere in this country. as long as folks move to where the jobs are or where tax treatment is better I think they kind of over look the adverse weather.

In what part of the country is it located?  

Ultimately, if the numbers make sense for your than move forward.I agree full heartedly…..but they are non-negotiable on their price.

I also agree with a lot of the comments you said about investing in CT.