And of course that brings the good with the bad...The RE industry by just its nature of being licensed self regulates it to a certain extent.. but when you get the monthly RE bulliten you will see many Licenses being punished or their licenses revoked for various offenses...

In this case there is a higher risk and therefor a obvious reason to reject.Investors get rewarded for taking chances, landlords get punished for taking chances.

Bad tenants need to be punished not rewarded for their behaviour.Next time do not use term lease.

The only exception to that is your case where it is a must have for the neighborhood and not having one severely punishes you when selling.

Self-manager that cares about their people: "..... decide to grant mercy or punish bad behavior if recurring ...I don't run around mailing and posting anything for the most part. 

After the loan closes, you know, live where you want...Failing to move into a property with a primary residence mortgage within 60 days is mortgage fraud... a felony punishable with prison time.Don't take this advice.

The thought process was to encourage on time payment vs punishing late.So example: 1800 (50 dollar discount for on early payment), 1850 due on the 5th.

If you are going to facilitate short term rental transactions in the city, make sure the transactions are legal, 'cuz otherwise you are "aiding and abetting" and can be punished. 

You may want to look into trusts based on what you're describing.Either way, I think personal improvement and working on financial literacy and responsibility will elicit faster and longer lasting change in a person than an external force requiring saving and doling out punishment if the rules are violated.

I guess I am taking my punishment well!