It's true, the sheer amount of plugins available is overwhelming. You might wanna consider messing around with the (Rea)plugins that come with Reaper. They should give you a good idea of what those plugins do in the first place. Apart from that it's like others have said: mainly trying out different stuff and discarding the awful ones. You might also make folders in the add fx tree, and drag and drop plugins in those. They don't get moved, they only show up in different places. I have folders like "EQ", "Saturation", "Drum VSTi" and so on. It's less easy to get lost in those long lists that way. Recently I've only tried out new plugins when I just couldn't seem to get a certain sound or application with the tried and true plugins I already have. What helped me a lot as well recently: when trying out new plugins (or going through my standard ones), I find a setting that sounds good (and maybe not too wild!) and hit the "+" button and go to "save preset as default". That way the next time I add that plugin to a track, it gives me a good starting point for further tweaking. Many many plugins have strange default settings that don't work in a mix at all. Of course you can also save other presets as well, might wanna name those clearly, so you know what they do :)