This tenant will certainly do more to "disturb the peace" of your relationship so in case they do pay the damages, do warn that this kind of disruptive behavior will not be tolerated and will be grounds for immediate lease termination. 

Well I'd say first consider things such as- how hands-on do you want to be, what is your risk tolerance, what is your ultimate goal with a property (do you want to work on it or just have it as a passive investment), etc.?

Sometimes the trade-off with longterm tenants is deciding whether to tolerate lower rents OR upgrading the unit with new floors, kitchen, etc.

Next there are more delays and more promises and before you know this is becomming a standard that you have learned to accept.In life as well as with investing: you get what you tolerate!

Those councilors have very little tolerance for bad behavior.Good luck.

Ultimately it’s a personal decision about your risk tolerance.

It has encountered stiff pushback from tenant advocates, for example, who argue it is exacerbating the housing shortage and driving up rents.So far most of the scrutiny has focused on rental apartments and homes that are converted to full-time vacation rentals, with regulators generally tolerating homeowners renting out a primary residence.There is a risk that could change.

For option 2), really depends on your risk tolerance.

The children came along and there was no tolerance for saving as the children were concerned.

NJ will not tolerate nonpayment.