This is for a 20th Anniversary milestone. We currently have a logo so we are not looking for a new logo. We are looking for one that emphasizes our 20 year milestone and the dates we have been in business. I like this logo but it needs to be modified to fit the overall objective of this project.
I would make Baker & O'Brien font size much larger than the 20th Anniversary. I think the 20th Anniversary font size is good. I would still increase the Baker & O'Brien though considerably. I think I like the design to the left of the logo as you had it initially but you might want to show both options. I really like the design though! I think that if the overall dimensions of the design are long and narrow that is fine. I really like both options though!