[Harmless Teddy Bear]

I would say that vandal is probably the subject with homeless being the adjective.

The sentence would make much more sense like this.

The 30 year old homeless vandal, with an extensive criminal history according to sources, was undeterred.

But news writers seem to think that dashes are cool and commas outdated.

[Tax-chick]

I think you’ve correctly identified what they meant to convey. Sigh.