Your good heart IS apt to make judgement errors. but don't let it totally harden you.

I was only 20 years old and he was a hardened criminal.

The longer we have rentals, the more we tend to "harden" them against tenant damage.

Like Richard we all hardened over time as that is really what is necessary to not only survive but to thrive in this business.

One way to tenant proof is hardening... another is finding out how to get a great tenant.

Further reading:http://www.biggerpockets.com/forums/52/topics/68041-how-do-you-harden-your-rentalshttp://www.biggerpockets.com/forums/311/topics/75451-bomb-proofing-rental-propertieshttp://www.biggerpockets.com/forums/52/topics/77534-rehabbing-for-rental-propertieshttp://www.biggerpockets.com/forums/52/topics/99325-how-to-make-your-property-indestructible-well-almost

You may need to put on several coats and wait the required time between coats in order to get it to harden - but in the end, you cannot beat the beauty of real hardwood. 

That hardened me a little bit, but I was still reluctant to even serve notices, afraid I would come across as a hard-a$$.  

In my opinion, repaints like that (sprayed or brushed) are for class C (and some B's) and below.It is sprayed by tradesmen who specialize in re-painting kitchen cabinets.If you use something like Sherwin Williams Super Paint (or even Emerald) Satin, or Benjamin Moore Ultra Spec Satin, it might no last as long as the pro-painter applied paints which have some kind of hardener in them.That being said, some tradesmen can do really nice work (with a lot more labor hours charged than on a standard rental unit respray): https://www.youtube.com/watch?

At least in the rougher areas, you can plan for this and rehab accordingly (harden units, use inexpensive materials  you expect to replace more often, etc.)