The existing laptop is a Thinkpad and for the most part it was a pretty good experience. I blame at least half of the issues that it had on what it is, which is essentially a 2nd/3rd gen netbook made more serious. By their very nature I don't think those products age particularly well so the fact that I got 5 years out of it is a pretty good sign. And sadly, for him, I've bothered Grawk with this type of stuff before.
I have given that some consideration but I'm concerned that it'll be one of those things that again, just doesn't work quite right as a result of trying to force something to be what it isn't.