Really depends on your use case though. If you're always going to be working on your own machine, of course customize it to make yourself maximally productive. But if you're regularly going into new situations, it's good to know how to be effective with tools you can count on being there.
My (admittedly very lame) anology: you're hiring a ninja assassin and have two candidates. One tells you about all the special swords and staffs and and smoke bombs he carries, the other says I just need my hands. Who do you hire?
I have a simple thought about this. If your work involves many machines, you usually have enough permissions to transfer your programs. I think that the benefits of a pleasant way of working outweigh the effort.
And by the way, I would prefer the first ninja if the second one is handless.
Like unix or linux? One person's "bucket of old shit" is another person's reliable swiss army knife that is always there when you need it.