Economic conditions have changed. 

If the city can eliminate an STR that has operated legally for 23 years, it certainly can change the rules to further restrict/limit STRs. 

I would not change them at all.. 

I think the hard part to assess is change in scenery.

Just need to set expectations for what you're actually getting in return, a small condo is not going to be life changing wealth.

If you make a couple of assumptions - i.e. rent in any given market is somewhere around 25%-30% cheaper than the cost of a monthly mortgage payment - you can find out pretty fast what's better for you.

If the ownership and the short-term rental’s street address have changed, you should submit a new application[8].

It appears to be a 'Dwelling, Single-Family Attached' so I'm not unclear if it changes the current zoning. 

This post is actually from 3 years ago, hopefully things might have not changed drastically in Sedalia by now.

Fast forward to now and my dad now flips homes full time and doesn't have to drive around the US anymore (he used to be a truck driver).