I had a 1x9 setup on a flat bar road bike (46T x 12/25 (or 11/26 for hilly rides)) and it worked nicely once I used the inner ring on the crank and had an aluminum chain guard on the outer spot. Did centuries on it, and had all the gearing I needed, and had good cadence options no matter where I was.

Your gearing sounds annoying to me, but it is all personal preference, as is the aesthetics. Your scissor worked chain dolphin, combined with the pie platter in the back, looks silly, IMO.

EDIT: what is the benefit of gaining 10 feet in a group ride? If it is a group ride, then isn't the purpose to be in the group?