If you follow this it should really help you mitigate a lot of issues when you are investing from afar.Don't buy in the roughest neighborhood in the urban core.

what i find though is in these rural low value assets a lot of the folks have quite a bit higher % margins than the highly competitive what everyone is chasing urban buy and hold in the quote un quote cash flow markets.. 

There are vast swings depending on the price-point and target audience that is most likely to frequent your STR.In general I see locations in the "hot spots" of the urban core leading to one norm in terms of occupancy trends and those near lifestyle locations and hospitals leading to a very different set of norms.  

I wouldn't say that Fitchburg is more or less desirable than downtown Madison - Downtown is great if you want to be more urban but if you move to the suburbs (Fitchburg, Middleton, etc) you'll get more square footage, garages, yards, bike trails, etc.

What regulatory barriers have you come across in such a urban market? 

Follow these tips and you'll probably be making a pretty safe investment.Don't buy in the roughest neighborhood in the urban core.

So what does a compassionate society do when it happens?

Or if they say things you don't deem good for society you take their privileges away.

In West Coast most urban area takes sometime and multiple adjustments to get interest. 

@Kevin Ivey I've been happy with Urban Enterprises.