It sounds like mistakes were made on the properties but I'm also questioning the market (you didn't say where these are). 

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. 

I have been narrowing down some markets and trying to explore/research more and network.

Thank you Lauren,  Yes, Pad split is already in this market so I think Im good.   

What strategies have worked best for marketing midterm rentals in secondary or smaller markets like Portsmouth?

As an aside, insurance companies are inspecting most properties one way or another in the current market. 

.🔹 Profit Multiple Ways – You can rent the property for cash flow, sell the option at a profit, or buy it later at a pre-agreed price (often below market value).🔹 Great for Sellers & Investors – Motivated sellers can turn a vacant or hard-to-sell property into income while investors secure future deals without a huge upfront commitment.🔹 Ideal in Any Market – Whether home prices are rising or falling, lease options allow you to lock in today’s price while benefiting from future appreciation.Other creative strategies—like seller financing, subject-to deals, and the BRRRR method—can also open doors, but lease options remain one of the most powerful, low-risk, minimal cash out-of-pocket ways to build a portfolio.

-why not pick a market closer to home? 

As the market evolves we've intensified our commitment to helping investors focus only on listings that are eligible for vacation rental usages and either; have exceptional existing production or high potential for rental performance.

We invest in every property type, in cities across the country, with different syndicators or private partners.