When it comes to web vs legacy applications, especially with modern JS libraries, webassembly, etc aside from a few niche cases which you have to basically struggle to defend, asking whether or not to start with web or ancient technology is like saying:
"Look, I know that cars are fast and everything, but they have a lot of up keep and there's so much going on with them and they're scary, so wouldn't you say that a horse and buggy are still a viable solution to travel with because I'm confused and/or intimidated by cars."
Or to put it more obvious: "Yes, web is easy to update, easy to secure, easy to keep it from being pirated, but I'd much rather have an application anyone can easily reverse engineer, lock out my updates, have to worry about a billion platforms or one single one where I still have to struggle with antiviruses, permissions, to the point where I act like Eaglesoft and just demand local admin rights for all users no matter what... sounds like web is great but, I heard serious applications are written with mud bricks, whoops, I mean old approaches because I don't know about jQuery and handling multiple browsers sounds impossible!"
Or in the case of the OP: web is about design and old applications are about whatever... let me hip you to something, all good web designers are terrible, terrible programmers. This is why these are typically two jobs. Yes, plenty of them defend how awesome they are at coding, how they care about standards, etc but if they actually let you see their code you'll find that either it's crappy code or a crappy design. That goes for both web and old style applications, it doesn't matter. Straight forward vs pretty.