Do you prefer to work with new tools or old ones? Do you always go for the best brands or go with the best value/price?
For me, generally I like to work with newer tools with the latest features. Although I love an old school drill and drop saw I've got. But I've also got a newer Makita drill which I find hard not to use.
I've inherited a few things from my old man which just haven't needed updating so keep pushing them til they give up on me. He used to do labour in exchange for tools instead of money as a kid and he still works with a lot of things he picked up way back in the day.