I've never made that many changes in my carry habits. When I first started carrying in ~2009, our family budget was exceptionally lean. If I bought a gun, I damn well just had to be happy with it, because there was no trading back and forth. That would have cost me money that my family couldn't have afforded. My first carry gun was a Springfield Armory GI model 1911. I carried in a Theis IWB initially, but decided that I also wanted an OWB leather holster for it, so I picked up a DeSantis Speed Scabbard. If you're going to carry a full-sized 1911 and an extra mag or two, that's a pretty comfortable way to go.
Still, it didn't take me long to figure out that there were days when it sure would be handy to have something to just slip in my pocket. Something for early morning runs to the grocery store, or when I'm working in the yard. So I horse-traded some stuff around and wound up with a Ruger LCR in .357, and put it into the rotation.
Well, after a while, I got to thinking that as much as I loved my 1911 (& I do), that thing got heavy if I carried it all day. This ol' fat boy is built for comfort, not for speed.... So I went to looking for something lighter. That meant polymer. To my mind, that was a bad thing. I'd never owned a polymer pistol and didn't really want one. Nonetheless, I've got some folks in my circle of acquaintances whom I consider to be pretty knowledgeable about guns, and they carried polymer pistols, so I figured I'd give polymer a go. Once I'd gotten past that mental roadblock, I re-examined caliber . . . . and decided that I didn't absolutely, positively have to carry "a caliber beginning with a 4."
So off I went to research another carry pistol, and I wound up with a Gen 4 G19. Pretty soon, she was getting more time on the belt than my 1911. After a while, I decided that it didn't make a lot of sense for me to have 3 carry pistols, one with a thumb safety and two without. So, with some sadness, I have mostly retired my 1911 from carry.
I haven't gathered the proverbial Box Of Holsters, but I do have one for each gun for almost any occasion, and every belt I own is a gunbelt. These days, I carry either the G19 or the LCR, depending on what that day's wardrobe looks like. I cannot always resist the siren song of the 1911, so I still carry her now and again.