Need to file a report against an individual for $400.  Documentation, essentially, as I don't expect much to come from it.
Can I then take that person to small claims court as well?  I'm not familiar with either, so I'm not sure of protocol.  If I can, do I wait for some sort of "resolution" on the police report, or can I essentially file both the same day?

You can do either or both.

On the amount I would ask myself if the hours its going to take to get a judgement is worth the time and effort.

No guarantee your going to get paid still.

I don't expect to get paid.  However, I feel the situation occurred as a result of an ongoing pattern of the person in question not being held accountable for their actions.  I guess it's a principle thing.

You can do both. My only concern would be both courts says that they are going to wait to see what the other court is going to decide. If there are $400 in damages, it would not be fair for both courts to issue $400 verdicts and you end up with $800.

The nice thing about a judgment in criminal court, is the court will collect all of the restitution money on your behalf and if the person does not pay on time they will get arrest warrants for failing to comply.