There's so much attention to detail beyond cleaning that contributes to the ideal "feel" and reaction to each property.

My first reaction to your question is that you should sell and put the capital elsewhere, mostly because your return on equity (ROE) is abysmal.

If you call customer service and don't get what you want, the first reaction is to ask to speak to a higher authority.

I am trying to picture my parents reaction if I made them sign a lease or sent them a late rent notice.

If you buy it, clearly it would be a rental given your wife's reaction. 

Rising rent is a reaction to an influx of people and industry/jobs to an area. 

I have never rented out my condo but may need to. is it bad form to post my listing on zillow or other platforms just to gauge the response and reaction to how desirable my unit is and what the rent expectations should be?

Sometimes, I also ask the agent/s about the buyer's reaction to certain characteristics of the house, etc.In some markets, upgraded/updated quality and condition make a big difference and others, not so much.

My reaction was only to that point.

So, my gut reaction is, yes.