I want to give this person a chance.The cons I see are: this individual has no savings, the individual's mother has an open court case that is being settled (she is not at fault) due to a car accident and ongoing medicals bills, they have one past eviction due to the accident preventing them from working for three months(they were asked to leave).

That being said I believe it prevents from big losses specifically from market adjustments - IMO 

A good mentor will prevent you from having that costly experience.

It is up to you if the late fee they are paying is worth it/sufficient.If you are not depending on timely payments (for example, if their rent is not paying your mortgage on the property), I say take the additional late fee income (I hope your late fee is substantial).When their lease comes up for renewal you might decide not to renew, you might leave rents the same or increase to whatever the market commands, but if you do renew I'd probably increase the late fee or restate your late rent policy to whatever you are more comfortable with.Keep in mind that charging a late fee does not prevent you from filing eviction.

As long as the buyer's agent discloses to the seller at the initial point of contact that he is an agent for a buyer, there is nothing from preventing him from speaking to the seller.

Sure a person can go digging and find out things but it prevents an easy list of all my properties.

I am kicking myself for a number of reasons on this deal, but the shoddy workmanship isn't really one of them that I feel would have been preventable if I was there. 

Unless there’s some emotional attachment to the house which prevents you from selling, get a realtor to estimate the value of selling as is and also ask their opinion on maximizing return.

A great agent will be able to help you negotiate a deal, provide you with referrals to great partnerships for your lender, inspector, and attorney and they'll prevent you from making costly mistakes.

Always have you or your representative there as well for two reasons.1) To protect your tenants belongings and privacy (There is no reason for a kitchensink repair to go into their bedroom etc)2) To prevent "Scope creep" with an issue.