I have investments in Hagerstown which is predominantly white where values are dust bowl ghetto numbers compared to Fredrick right down the road.

What one plumber charges compared to another doesnt matter .  

This means I'd live part time in Big Sky with my partner for awhile until finding a comparable job in that area. 

So for instance, lets say the mortgage is $3400 flat and that split amongst 5 people would be $680 but I was thinking about raising the price per person to $750. 750x4(roommates excluding me)=$3000 leading me to only pay 400$ month compared to paying the full $3400 by myself.

There are an awful lot of threads on BP asking about property manager pricing, so I generated a spreadsheet tool to help investors compare pricing for management companies. 

And then, you'd have to deal with the locals as a gringo so you are at a disadvantage compared to the locals and you could be taken advantage of.

Whatever you call it, you’re comparing different investments based on their yield.Another way to look at this is to think of IRR as the rate needed to convert the sum of all future cash flow to equal your initial investment.

Pricing is typically comparable to the online sites. 

If you believe hiring someone would be cheaper compared to when you do the job and include your time, I would say hire a handyman.

Obviously rent goes up as price goes up but at some point it just isn't a great investment compared to what you can get in the lower price bands.