I generally would not invest in a place that is declining in population but if you are going to live there then there can be exceptions.  

Quote from @Kaleb Johnson: Quote from @Brandon Vukelich: @Kaleb Johnson if you are serious about wholesaling, it is highly recommended that you hire a real estate attorney in your state to help you draft the docs you need, applicable in your state.

Residential investing is not rocket science, knowledge is not the issue: there are many good books out there that walk you through every detail you need to know.

Brian,Because VT is a traditional rental market (ski houses), depending on the minimum duration you will be allowing for rentals (ie. monthly, Weekly, etc.) there are some regular carriers in the New England Market that will write it. 

What are we overlooking?

Considering that my parents and I are not Canadian citizens it adds an additional wrinkle to things as they or I are not able to claim this as the primary residence and avoid the capitol gains tax... a lot to consider and think about.

The court would not grant that, unless there has been provable, recent abuse of the bankruptcy process by that individual. 

Our current plan is to purchase our first home and live in it for 2-4 years before moving to a new home and using this first property as a rental, so my fiance and I are currently in the market for a home that we could use as our residence during the offseason and then use as a short term rental or something like that while we are away for 6-7 months.

Residential RE is based on what your neighbors pay so if you are all in less than they are every time you are doing well

If you are out of money on this, it's time for creativity and elbow grease!