I just use laptops now mostly so I usually don't try and update it anymore. I just buy a new one every four or five years and that's only if it really does slow down by that much. I prefer to just buy more pensive laptops which last longer if I can but if at the time I don't have enough money then I don't have much of an option but go for the cheaper ones.
It would depend on how badly you need the upgrade. I don't upgrade parts just because they're outdated, no that would be cost efficient since almost every year there would be a new one. If the part is not doing what it should do anymore or if you can't follow on deadlines because of your computer then it's time to upgrade.
I have not done that till now and I believe a lot of people usually do not do it. I think it is best if we try and upgrade it when a better version of Windows. I should think about doing that very soon but I guess I am quite scared right now.
I normally replace the Laptop every 4 years and that almost closely coincides with MS updating its OS. This time I might have to do it early as mine fell down and the hinge broke down and looks like MS is updating their OS too.
There's a saying, "if ain't broken, dont change it." Since I first owned a PC, I maximized it use until it was no longer able to cope up with the requirement of the software. I find it useless to upgrade some parts and other parts left behind so I make it a point that when it is time to upgrade... the whole old unit should go and replaced with a brand new machine.
I'm still in the process of building my desktop and it'll be something I continue to do moving forward. To me, there's no better option than building your desktop as you don't have to shell out a lot of money at once and can buy it in pieces. And when you do buy new pieces to the computer, you can always get the latest gear to be sure it's the best out there. As far as laptops go, I'll usually go 2 and half-3 years before I need a new one. It's around that time it starts getting slow and battery life doesn't last very long, even on new ones.
I have the same desktop for 10 years now still running XP. I spent the extra money at the time and got the better processor and mother board (Core2duo e6600 and dg965ot. Looked it up so many times I've actually memorized it lol.) Still runs really well.
I can't afford spending countless amounts of money for a PC which becomes old in a relatively short amount of time, so I prefer spending around $500 each 2 years for a new one powered with the latest gimmicks, so that would imply me saving $250 each year, which is fairly reasonable compared to my possibilities and resources.
I generally update my PC as needed for my workload/leisure activities. Being a somewhat avid gamer I generally look to upgrade most parts every 2-3 years. I can do this relatively cheaply by first building the computer myself and secondly by figuring out which product I want and then aggressively searching out sales/discounts on the product. Funnily enough my consistently upgrading attitude with desktops is opposite to my attitude with laptops; which is pretty much to get an old one and just use it until I can no longer fix it, then trash it and get another old one. My laptop is generally only used for light browsing, Microsoft Office programs and Mathematica/Maple for school. I do really have to stop slacking on my monitor choice though as the two I have now are beginning to show their age and use.