I have a shitty bike that I bought for 150 € ten years ago. It creaks everywhere, is hard to ride, and a thief once actually moved it out of the way to steal the bike behind it.
I use it every day but I'm not going to get a better one, because I don't want to be constantly worried that someone will steal it. I want to use it as transportation, leave it wherever, and know that it will still be there because it's not worth stealing.
Plus, being hard to ride means I get extra exercise for my fixed-length rides.
A couple of years ago, I've found a gem of a bike. It looked maybe 15-20 years old and was clearly heavily used - frame was full of scratches and such. The color scheme was pretty ugly and was just a tad too small for an adult. But I noticed that all the components were actually decent - mostly Shimano XT, obviously very old models. After servicing it, it rode very well and I didn't have to worry about thiefs since it was pretty cheap and even more cheap looking. I still locked it, but the peace of mind was nice.
Related, when I had to live in a certain area that had a high bike theft rate, I got myself a pink bicycle. In the year I was there, it was never stolen. Well, except for the seat (which was black).
I use it every day but I'm not going to get a better one, because I don't want to be constantly worried that someone will steal it. I want to use it as transportation, leave it wherever, and know that it will still be there because it's not worth stealing.
Plus, being hard to ride means I get extra exercise for my fixed-length rides.