Over the last 30+ years, I've gotten pretty wound up at times over the actions (or sometimes lack of action) taken by tenants.We all have to remember, it's a business. 

Adding in legal fees feels like salt in the wound.

Established professionally, financially and house and kids.At that stage of the game in my 20's I would dump every ounce of extra cash into a domestic small cap/ S&P mix fund and not look at it until I established myself and saw investment opportunities which cash-flowed, and I likely would have wound up right where I am :). 

(Side note - Don't take this the wrong way but based on the language in the last line of your post, I don't think you're ready to be getting yourself wound up in a deal like this.

I did that once only after the parents cosigned, that ended up being a rock band.They turned the basement into a recording studio.The front door was trashed the place look tired after they left so I kept three deposit licked my wounds and moved on.The best part I went to you Tube listened their music that was cut in my basement.

They really have been great tenants.Would it make sense to raise the rent slightly to help offset the greater risk on my part, or would that seem like putting salt on the wound since he just lost his job?

Some of my best deals wound up being 25% of the original asking price.

She wound up getting prosecuted for it.

Also my deal wound up costing me way more up front cost than expected.

He threatened to take a hammer to the job and wound up having a sheriff standby to see him off the property.Never again