However, a lot of concerns can be mitigated with looking at their past rental behavior in a lot of different settings.

These 2 platforms don't focus on MTR but vacation rentals so using Furnished Finder is a better way to get those longer term folks.I have always been a bit concerned about the area's penchant for restrictions.

As far as rate is concerned, you can usually go about two points over the current rate (less closing costs for a seller financed deal so there is no real expense there) You need to make sure the borrower can cover that.

Even if I were to rent it out on Airbnb, the cash-on-cash return isn't very attractive.Specifically, I’m concerned about:High mortgage payments and the financial strain it could cause if the property doesn't generate sufficient cash flow.Cash-on-cash return is low, even with high-revenue short-term rentals.My Questions:Risk Mitigation:Any strategies I can use to mitigate the risks associated with owning a high-value property with a large mortgage?

There are risk so to gloss over those risk for the sake of selling mentorships is concerning. exactly Joe.. 

My concern is with the house that my dti numbers will remove my options for a loan.

That’s a major concern.

yeah the tenant pushing back is my concern. it just so happened that this happened with the tenant that seems to not like paying. and the heating is electric and this winter has been extremely cold which caused the electric bill to jump up to $800!

Can you please help me understand better what potential concerns in your experience can potentially arise here? 

I'm not concerned about his being able to make the payments and trust him to do so.