Trade Dress Protection: utility vs design patent strategy

I publish illustrative scenarios prepared by my practice. All participants and conversations are fictional. The fictional posts are not posts by real users, accounts of client experiences, or reports of actual results.
Illustrative scenario prepared by my practice.
For informational purposes only. This is not legal advice. Laws vary by jurisdiction. Consult a qualified attorney for advice specific to your situation.
Hypothetical question

Sorry for the wall of text. I'm in a difficult situation and trying to figure out my next steps.

utility vs design patent strategy. I've been dealing with this for about 3 months now and the situation isn't improving.

I have already done some research online but got conflicting advice.

What are the risks if I pursue this? What's the likely timeline?