Yes, you should file a report with your local police precinct. They could be criminally liable and be charged with criminal mischief.

What consequences will my boyfriend face?

Need more facts to properly answer your question. The bail amount ($50,000.00), on its face, seems to be relatively high, especially given his age...

Could the judge say jail time?

The Judge would probably not change the plea agreement unless you violate any terms of the plea. You may be subject to jail time if you get...