Selling it.Shortly after some zoning changes came into affect that would have permitted triplexes to be built on both lots.

Markets I'm interested in are the Chicago suburbs, Milwaukee suburbs, Las Vegas, and eventually Los Angeles when money permits.

The licensed pllumber pulls their own permits, the elctrician pulls their own permits.   

Were all of the renovations you did in the past permitted correctly or DIY?

Check local regulations.First, verify that your local zoning laws, HOA rules, or condo bylaws permit renting your property.2.

First thing to do is check with the city or county to make sure the ADU would be permitted to be a STR.

For instance, in New York State, it's not permitted to collect last month's rent, additional security deposits beyond one month's rent, or pet deposits.Regarding the carpet issue, even tenants without pets can sometimes leave carpets in less-than-ideal condition after a couple of years.

You know how to get your permits.

Rethinking density limitations like building height, parking requirements, and ADU permitting would be more impactful. 

Timing your permits and applications might be tricky.