The only thing I recommend is Pathogen which keeps addons modular. From there only add things to the baseline as needed.
I tried switching to Ubuntu from OSX as many times as I tried abandoning Textmate for VIM.
The thing that made me finally keep using Linux was using a very stripped down version called "Arch Linux". This made me appreciate the basic fundamentals of the operating system, with no fluff [1].
It was rough around the edges at first but you learn how to deal with quickly.
I eventually switched to larger and easier-to-use Linux distros like Fedora/Debian. But whenever I run into problems with them, I have the experience to understand/fix it from working with Arch.
I now have no interest in going back to OSX and use VIM obsessively.
Many comedians will say this too: the only way to get motivated to be successful is with your back against the wall. Being partially comfortable makes you complacent.
That means incrementally building up your array of useful plugins and not installing them all at once. You want to be very selective about plugins in general anyway, and pay attention to which ones are the most useful to programmers who get a lot done, which will make you want to try them (I'm thinking NERDTree and Ctrl-P here).