If they find out, they can get really intrusive and they do not care about your circumstance.

Instead of lawn care, you have snow removal. 

1) If you continue waiting for the "right time ”, you’ll always be waiting.2) Your current job doesn't care about you.

Be careful about using your current home equity as a down payment on another property.

If the covenant specifically prohibits renting out rooms or STRs, you may be restricted from doing so.You should carefully review the covenants tied to your property to understand the specific restrictions.

They said they couldn't identify an IRA as the owner of an account and were uncomfortable with this unconventional request. 

Can we just take care of this at the time of the sale? 

However if it’s a really big hazard and they fail to take care of it quickly, I might just take care of it myself rather than taking any legal action, personally.

One thing I did note is my insurance is $3K a year lower due to the monitored fire suppression system in these larger properties versus my smaller properties that sleep 12 or less built close to the same time.As someone who has lived in Illinois twice, the politicians there don't care if people burn as long as they can tax and spend. 

The cash flow is poor for this value of an asset and my equity position.