., zoning issues, etc.Is there an agent that understands that market?

Are there any red flags or major pitfalls I should look out for as I proceed?

These are areas in a state of flux that can either become better areas over time and the investor wins big or they can fall back into war zones again.I see that as gambling and if you do that you might only want to make it a very small fraction of your overall net worth to invest.

Another tip I have learned is attending/listening to county zoning meetings.

A few months ago we accepted a second roommate, ignoring some red flags on her rental history because we needed the extra monthly income.

@Tyler Brown, the argument for keeping that property is if it's in a zone of appreciation and a time of appreciation. 

Trying to figure out how to declare on my personal taxes without causing any red flags.  

Are these red flags or should I still send an offer any way?

Check with your local county tax collector, zoning and code enforcement.

I wonder how the snow zone can give positive cash flow with lot of headaches around maintenance.Thanks for reply!