hehe, I am going to take a guess that you are under 50? Later on, "cool" matters less, you go with whatever's most fun for the limited time you have left to chase it.
Our crew are long-time surfers, who got into kiting to deal with the windy days as the surfing is no good. We have now probably 75% switched over to wing, not because kiting is no good, but partially because winging is something new to mix it up, but mainly because foiling optimizes crappy surf. I see winging mainly as as surf/wave/swell riding tool ... flat water, you may as well be kiting (assuming decent wind and good launches). I do miss schwacking lips and do intend to get back on the kitesurfboard. Similarly, I miss the jet powered skateboard feel of the mako twintip, along with those lifty weightless airs....also intend to do that. And going crazy fast on a kite foilboard in barely any wind. All of these things are fun on the right day.
So, forget your cab or economy rental, you need a sprinter van or a trailer to pack all the gear.