Ask HN: Windows software discovery

I use OSX and Linux at home, and OSX at my previous job.

I have to use Windows 7 at work to use proprietary software for a laser cutter.

My issue is this: how do I find Windows utilities that work and are clean. Three monitor setup is nice. I do a lot of 2D car work, so I use AutoHotKey for macros etc, have a 19 button Razar Naga mouse.

I want to find a good light weight utility to make windows always stay on top and be transparent. Also looking for a decent light weight streaming radio ripper.

Finding software for OSX has been easy for me, there's almost always one or two clear winners in the free / open source realm and another one or two really good reputable apps in the paid-software world. Hasn't been so easy for me on Windows.

Any help would be greatly appreciated.