Macs in 98 are a fairly different beast than what they are today. You are right, incompatibility is no longer an issue for almost everything. If you live in calgary you could set up an appointment at the apple store and get them to show him the positives. If he still doesn't see the point then perhaps it wouldn't be best to push him. I'm a major mac fan but they are different and depending on how used to pc's he is the transition could be frustrating. I'd make sure he's on board before a big purchase.
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