When I'm motivated, I can come up with the right thing to say and the right way to say it. I think having a few days to think over how I was going to present the new computer purchase to the Boss helped me phrase it in the most judicious manner.
How does this sound: I've come up with a way to upgrade the computer without buying a whole new system.
Or this: Some of the hardware on our old computer is breaking down, but my nephew is going to help us salvage what we can. That way we can have an up-to-date system for less than a thousand dollars. (Kind of a magic number with him.)
What astonished me is that when I told him how old the current computer is (three and a half years), even he, the very model of a computer illiterate, was surprised. "Really?" he said, as if he knew all the implications of running a business on a machine that many generations out of date.
He told me that part of the way the business works is by keeping me happy with the tools I use. When he needs a new table saw (or a new forward-reach forklift, for that matter), he buys one. And even though the speed and power of the new computer will benefit me (and my DSL) much more than it will him (since I rarely do anything for the company that isn't a word processing document or a simple spreadsheet), he seemed happy to spend the money.
I didn't tell him, of course, that he'd already spent the money, since I ordered the new machine yesterday.