I see off market properties weekly, talk to investors both new and seasoned daily and I am actively buying myself.

Lenders do not look at your personal income or debt and will use the current market rent or lease (up to 120% if the lease is significantly higher than market rent or vice versa) as qualifying income.

In a highly competitive tourist market like New Orleans, I update my photos weekly. 

Highly recommend partnering with a local realtor who knows the market. 

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

Here’s our OPINION for the Metro Detroit market (use as a template for your target area!)

Try networking locally with HML's who know the market. 

For now, I'm mostly focused on identifying the right markets.

on the one hand, if you're happy with it, and you believe in this market, and this is what you wanted, great. the fact that you're asking the question shows that you're being thoughtful about it.with that said, it sounds like you're into the deal for almost $90K out of pocket, and so if you asked me if i would put $90K of my hard earned cash into a property to get $175 month, the answer is no. 

It requires no money upfront, so you will join thousands of others trying to do the same in your market.