Property in Ohio is cheaper than where you live because it’s less desirable and will always attract less desirable tenants with higher maintenance and more evictions.

First, increase staff size.

The 4% isn't much, but it's better than nothing and it means my security deposits increases with rent each year. 

A shorter minimum stay and dynamic pricing are great for attracting bookings during slower periods, though the trade-off with single-night weekend stays is definitely a balancing act.

In the past year or two we see lots of rentals and investors and rent prices have not kept up with home price increases. 

You'll figure out a good price for yours, but be sure to check the market every month or so, and track whether it is increasing, stabilizing, or decreasing.

This has become challenging due to an increased interest in the historic district in Dubuque due to revitalization plans that include 18 million dollar investment into the historic downtown area. 

For that time frame it would not make sense to turn it into a STR as there won't be enough time to establish a history to attract good vacationers.

If the answer is "close enough," they move forward without much hesitation.While it's true that higher-quality tenants are easier to attract with nicer homes in better areas, I’ve managed C-class properties and had fantastic tenants.

I'd try to get a 6-month lease at a below-market rate to attract a tenant.