The STR market here has become way more saturated and competitive especially in San Juan. 

So it could take a decade to get to todays market rent. 2) it’s almost impossible if not impossible to non-renew a tenant, especially if you’re not an owner occupant. 3) As a seller, even if I could remove paying tenants I never would without a non-refundable payment from a potential buyer that covers all vacancies for 6 months if they fail to complete the purchase. 4) You MIGHT say as a buyer that’s worth it.

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

There are really great REI opportunities in different markets - markets in the Midwest and Southeast of the country are particularly lucrative - where not only are the purchase prices reasonable for most RE investors, but the homes are turnkey (new builds or completely rehabbed homes, tenant ready, systems 10 years of life remaining on them, property management teams in place) with appreciating home value AND appreciating rent.

Some renters may hesitate, but if the rental market is strong and insurance is covered in your numbers, it can still work.

Mine have appreciated off of the charts in the Charlotte metro market.

We weren't super happy with anything we were seeing on the market, so my husband and I had just started writing letters and looking off-market... until we saw this property.It'd been sitting on the market for months.

Since I'm based in Tampa, I don't look outside and compare markets. 

Much like other markets in the Midwest, investors go to our market because of the low barrier to entry.

An ADU could rent for an additional $1,200–$2,000/month, depending on the local market, potentially doubling the property's cash flow.