Brad, sorry you have to do that. I've had to evict two tenants in five years. The key, IMO and experience, is in how you present it to them and to actually avoid legal proceedings.
I've done this using the easy vs. difficult presentation to them. The key is to tell them they WILL be vacating either the easy way or the difficult way.
You tell them they must vacate and do no damage then you will not take legal action against them (I call this the easy option) and you will then either allow them to use their deposit against what they owe you and/or set up a "promissory note" payment plan - which is enforceable by law. The key here is it will not go against their record.
However, you present option #2 - the difficult plan. You will have the sheriff out in five days to remove them and you will take legal action against them to recover back rent, any damages and the cost of legal action. And, this will tarnish their record.
One of the keys to this is putting everything in writing and posting it on their door and taking a picture of it posted on their door and then sending them a text of the picture with an explanation. You MUST document!
Best of luck.