Nina will definitely be the one to make the call on many of your questions. In my personal opinion, I'd recommend something without the elastic stretch side panels commonly found on chelsea boots. When you take a longer stride walking, people will likely see more than just the toe of your boot. It is Nina and the LMO crew's final say, but I'd recommend a boot that has a smooth solid black appearance at least up to your ankle.
The recent saber photo that you posted looks even better than sources I've found in the past, bummer that they are on an unknown hiatus.
When we originally submitted photos, I made sure Nina had access to photos, but I originally went through my GML who worked with NIna and the LMO staff for approvals.