Agricultural land and property suitable for residential development seem like safe options to me.

The rents were much lower than I originally estimated, which was a bummer.

Should I wait for Spring for greater inventory, or for lower rates to see if cashflow improves?

I would like to find a way to generate additional income and am exploring options other than having a long-term roommate.

You'll find most HMLs will use lower operating expense margin when they underwrite a DSCR loan as they usually only factor in taxes and insurance. 

The planning staff should be able to walk you through any options for zoning changes or variances if there's a way to make short-term rentals work in your case.

While you likely won’t owe taxes due to the loss, filing is still required since the rental property is located in Missouri.Kansas (KS): As a Kansas resident, report the rental loss on your KS state return (KS-40) since Kansas taxes your worldwide income, including out-of-state rental activity.Tax Impact: The rental loss reduces your federal taxable income and may lower your overall state tax liability.

As another poster mentioned rates are lower than they've been in the previous 18+ months but unless some very surprising economic data comes out between now and when you did your refi it seems unlikely that rates are going up in the short term and there is at least a decent chance that rates drop a little more before then. 

Have been exploring other options as well.

Mashvisor – Helps compare long-term vs. short-term rental potential, especially useful if you’re weighing both options. 4.