Mortgage rates make buying a permanent residence painful and costly... 

I would prefer to do the upgrades so that it gives the property a permanent higher monthly income and hence higher evaluation if I choose to sell. 

Then, after completing repairs and stabilizing the tenants I would refinance onto permanent financing.

In the event of a true disaster, just know you can't keep yourself whole.Basically, you're participating to save on pennies--via a normal insurance process--and to keep yourself exposed to any fat tails event. 

There are a lot of different ways to start investing, so trimming the fat on the direction is a great beginning. 

We're looking to add something in this area as a 2nd home once we're a little older and closer to retirement and are looking to buy something that we can rent 90% of the time until the time comes to move down there on a more permanent basis.

@Sailin Li I am in the Gig Harbor, WA area and the city council has passed a temporary ban (trying to make it permanent) against STR.

I don't know the laws of New Hampshire but most property law prohibits land locking property, meaning all parcels must have some form of legal access from public space to the property, whether through a permanent right of way, narrow deeded entry, or something similar. 

I think maybe our family has reached the tipping point where it's wortwhile.JThink about something very bad happening at your property (think fatality or permanent disabilities) and then ask yourself what an attorney might sue you for in that type of scenario.  

For example, take a fat food franchise.