I like OP's way of thinking...and this is very much why I have so many cameras. Most of the time if I am actually going on a photo walk, holiday or international trip I am happy to carry a camera bag with relatively sophisticated cameras. Other times I just feel I'd rather bring out some 1930s base model camera, for the hell of it, and wander around town shooting buildings and street scenes. If course occasionally I do something slightly insane like deciding that a Zeiss-Ikon folder is the perfect instrument for the summit of Mount Etna in winter....but then, I was right! It was!
Some years ago I watched a short documentary, probably on BBC TV, about a photographer who wished to prove that it was the skills of the practitioner and not the tools which were most important. He set himself the task to take a photograph of the Queen on an old box camera and get it published in a national newspaper. We were already in the digital age....so at the event in question he was jostled among the other pro photographers with their DSLRs, long lenses and burst shooting capability.....there he was with his 120 film and 8 exposures maximum. He reeled off his 8 shots, ran to the nearest 1 hour photo shop (there were still a few around then) and got his film developed & scanned to a CD-ROM....and then started hawking his photos to newspapers....and yes, he got one really good shot of the queen on that box camera and it was published in The Sun.
Curiously, as a musician I only have one violin. Though I certainly appreciate the difference in feel, look and tone of different instruments. Usually when I go to a gig, the guitarist will have at least 3 or 4 guitars on hand....likewise some of us will have many cameras. I'm going camping this weekend. The Zeiss folder is a no-brainer as I have an unfinished film in it....but as for a 35mm camera....Yashica Minister III? Agfa Super Silette? Konica Off-Road? Lomo Konstruktor? Ooooh choices....