People who are involved in anything tend to have an overinflated sense of self, ego and importance.

We have several subcontractors that handle the process but the owner has zero involvement.

Add to that the fact that private financing typically involves way less bureaucracy, with reduced paperwork and fewer hoops to jump through.

Of course, you would need to do your own research and due diligence when purchasing a company but perhaps that's a way to get involved in the trades in the owners seat.

Now, if they don't want to do that for whatever reason and don't have anybody to work with who would do that for you, I'd have to agree with you that they'd better invest at home rather than getting involved in something they don't understand.

In the case of my 16 unit there were no realtors involved.

In a tenant friendly state you have to.BTW, when you list, there's a fair housing law. you cannot deny a sec 8 if they qualify. your standards need to be the same for everyone

Undoubtedly, the biggest regret is getting involved in the short-term rental market.

In that case you should get an attorney involved as encroachment would be a material issue that if known should have been disclosed both to the broker and to any potential buyer.  

Keep in mind magistrates deal with MANY MANY cases involving small issues so their rulings OFTEN may not follow the correct technical application of the law.