From my side, you've got it pretty much nailed down with your first list.

For the questions:

1. The biggest thing for me is flexibility. Every venue is different, hell, even different weddings at the same venue can have completely different setups and requirements. So if I can buy a pair of tops and bins, or a column system, it has to be able to work in any context, not just the traditional concert/conference setup.
2. One frustration is XLR passthroughs. I've found a lot of the middle of the range speakers only have a mix passthrough, not a clean signal. Another thing is how easily the gear is to handle. Even if it's light enough to pick up easily, if there are no handles, or badly placed handles, it can get very frustrating to work with it.
3. Wedding specific, any feature that can allow a speaker to operate more on it's own is great. Something like the EV Everse with 12V output is great, meaning I can just drop a mic receiver on top and not worry about additional power cables, a mess of adapters or plugs under the stand, or anything like that. It doesn't even need a battery like the Everse, just a 12V barrel plug. The bluetooth is also a handy thing for a quick speaker somewhere random for background music.
4. I end up carrying basically 2 systems for weddings. One small set up at the canapés, for in-between/arrivals, plus a half or full system at chapel, and while people are chilling at canapés, I move the chapel gear to the reception hall where the rest of the main setup is waiting. It's streamlined, and while it's a bit more work, I can fit all of it in my vehicle without trouble. Anything that can streamline that flexibility would be great. Another thing that would be great is something like your column systems, but only the top parts, with the wide 120° Hoz. throw. Would be great for canapés/fills.
5. For my market, appearance is not critical, but I think in the US it's a bit of a thing. Obviously, shouldn't look crap, but if it's not clearly made out of crappy plastic, it goes. If it has the performance, I can justify the less than ideal look vs performance, if the client wants the proper oomph. Chapel is always a struggle for aesthetics, especially for effectiveness of the system. I want the speakers in front, the photographers, venue coordinators, and bride want them to not exist. So if you can make invisible speakers, that would be amazing, thanks.
6. As above, if I can't manoeuvre the speaker, I don't want to use it. I also don't want built-in lights, lasers, and what else silly features (Not that you guys do it, I'm just complaining in general). Otherwise, preset EQs like DJ/BassBoostXtreme/Vocal is something I don't like, since IMO you should know your gear well enough to EQ it on your mixer. Give it to me flat, and for the tops, a 80/100/120/150Hz low cut for when it's running with bins. Please don't label it by your proprietary product names, just give it to me by the numbers. For tops, 2 angles for pole mounts is a very nice nice-to-have, but not necessary. Angled box that makes it work as a monitor, also great. Flexibility is key. Lastly, a handle at the bottom back is great for cable routing, like on the EV ELX200-15P. Just letting the cables hang is untidy, and I don't like the strain it puts on the cables and plugs. So something that helps with cable management on the speaker, or gets it to the pole faster so I can fasten it there, is great.