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

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

They may favor buyers who demonstrate a willingness to use the property in a way that aligns with their values.Pricing: Non-profits might prioritize achieving fair market value, as they have fiduciary duties to maximize value for their mission.

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

Here’s why this market is so ripe:1️⃣ Mom-and-Pop Sell-Offs at Huge DiscountsA lot of these properties have been in the same family for decades, but now the kids aren’t interested in taking over the business or the real estate.

I recently bought a commercial condo (retail) and have been going through hoops with the seller (developer) to make changes to make the space ADA compliant. 

Am I getting greedy to ask for an additional seller credit at closing to help offset some of repairs needed?

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.

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