If you are taking care of things, any punitive damages would zero or very small.

Instead of lawn care, you have snow removal. 

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.

I say, if everyone is talking about it, it's probably too late.Be careful not to reject someone's advice in a city you haven't heard of much.

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

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

This probably implies FIRE in his 20s, but I hope he is passionate about the path he has chosen and excels at it until at least a more traditional retirement age.He started the 2nd rehab he is leading.  

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

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

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.