The tech will do it,along with transferring my data files, included in the $350 he quoted. Unfortunately, he will not install my software (Can't blame him, I'm not looking forward to it either).
If Win7, then...
Since you are paying him to do it, make sure everything works. He should test it but might miss something.
The tricky thing with older computers is that there might not be a driver for all of the hardware — video card, wifi, usb ports, etc. etc.