I stopped using Winrar because it's so rare that I use rars anymore. When I compress stuff, it's usually more to turn millions of files into a couple of hundred files (I have a lot of manga on my computer). Don't really care how good the compression is in that case so I use zips since it's directly supported by windows. The few times I need to extract rars I just use 7zip since it's not always bugging me to buy a license.
I bought WinRAR awhile back, so I don't get the pleading for (more) money.

My compression is usually to turn lots of large files into long-term archives. WinRAR's better compression helps with that sort of thing. It's also nice sometimes because having a file as an RAR means that Windows Search
won't be taking up lots of time looking through the contents of every compressed archive I have.
I stopped using winamp when they decided to put a browser in their player. I don't need one bloated program to do everything, and the moment a company starts moving in that direction I generally stop using their product. Foobar just works and is incredibly lightweight with a cleaner UI by default.
I didn't even know that was there. I'm still using the Classic interface. The fancy new interface was indeed bloated, and back when I had a non-SSD hard drive, it took longer to load.
I'll have to give Foobar a shot again. I tried it a few years ago, but I don't remember anymore why I opted not to use it.