For number 3 you are saving time with a big kite. Years ago I had a 21.5m Cabrinha Blacktip with a leading edge about a foot in diameter. It saved time and energy pumping that beast up. Now I use an electric pump for my 16m xbow and to preinflate my 21m FS. Besides I'm getting old and I need all my energy for riding...
I think I called out WMFG previously on proprietary hose and proprietary nozzles. Life's too short for proprietary solutions and greed is not an excuse for that. They're not the best and I'd encourage everyone to not buy one. I use Singshot tall pump though.
Overall I don't enjoy inflating the kites but I can say that I saw more than enough pictures of girls smiling wide, butt an boobs sticking out, while obviously enjoying pumping the kite. We all need to learn their attitude and focus less on technicalities.
I couldn't change my attitude but fortunately foiling moved me to ride smaller sizes and pumping a 5m-7m-9m wings is not that bad of a deal with any pump.