I like to upgrade every 2-3 years, at least my box. I seem to be able to get a monitor to last longer...
My approach is to buy last years technology that is closing out at good prices today. The advantage for me is that I'm upgrading steadily, but not at the cost of buying today's latest and greatest machines. Also, I'm not the guinea pig having to discover and work out the bugs on the "latest and greatest". I like to watch the forums and reviews and see what others' experiences are, so I can make an educated choice when I DO purchase something. I like the reviews from regular users, in addtion to the "official" reviewers. I'm not so sure about the new operating system that's coming... (I hear there may be some tradeoffs) but I know what to expect from XP and it works great as far as I'm concerned. Is the new operating system something really good for us users? or is it just another way for companies to make a ton more money?
I think waiting a long time and trying to get the "perfect" machine is like torture, and puts too much weight on the decision. I don't need my decision to last 5 or 10 years. I know I'm going to be upgrading again in a couple of years, or maybe sooner if it turns out one of the newer machines has a feature I really like. The reality for me has been that the newer machines have some gains but also some losses, like you mentioned... losing the use of some old software that you like, but the new systems don't support. Gains in processing speed and storage space can be irrelevant if your favorite software won't even run on the system.
As others have mentioned, it really depends on what you want to accomplish. How much money do you have to spend? I figure on about around $300/year keeps me moving forward technologically at what feels like a cost I'm willing to pay. At that rate, I don't feel so bad if the system I get isn't "perfect", plus, I know it's temporary.
Right now, I have my eye on the Emachines AMD64 3500+ machine. It packs a lot of power for the price. It was being demonstrated at Best Buy one day, running one of the most popular war games with ease. This machine, with a meg of ram was available for around $500. For my money, that's a LOT of computing power. If money were no object, I'd shoot for a more advanced gamers machine with the specialty graphics card etc. I'd expect to spend over a $1000 for such a machine. But I wouldn't expect to upgrade this type of machine every other year like I do with the less expensive ones I buy.
By the way, Emachines have had some challenges with reliability in the past, but they have gotten a lot better in recent years. Personally, I've owned a couple with only minor problems with heavy usage. I have no problem buying that brand if it's great value. If HP has a machine that matches up and it's only slightly more..... I would go with HP. I like HP. My current box is a Compaq, my 3rd Compaq, and it's fine, too.
Finally, I wouldn't ever buy used when there are such great deals on excellent systems being closed out to make way for the "latest and greatest".
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