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

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?

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

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

In many/most places you can pull permits and do work on your primary residence yourself, but you need to be a contractor licensed/insured to do that in the rental units.

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

Funny thing about builders, they don’t want to invest that much time into you until you are ready to go the the permit phase. the same bank that gave me the land loan is also prepared to give me the construction loan.  

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

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.