Exactly why do you “need” to upgrade those items every couple of years, and list how the new versions were so materially different for your work that it was necessary?
So first of all as a freelancer, speed is a significant factor. If it takes me twice as long to do something due to equipment then I will either be priced out or have to drop my rates. Also, software developers add new features which are only supported on new machines. Again, this is a case of adopt the new tools or fall behind.
1) Main computer - I've been running a late 2013 iMac which was okay - a bit slow but not unusable (it was a built to order unit, i7, 32GB ram). However, even though the spec on this was better than later machines, Apple couldn't be bothered to do the work to support the BTO machines and so any late 2013 iMac would no longer have major OS updates after 2020. This meant I couldn't update other apps I use on a daily basis. Photoshop had not updated for the past 3 years meaning I was missing out on new features which improve speed and workflow. Significant improvements to content aware fill and the addition of generative fill have dramatically decreased time spent on editing assets supplied by clients I often get sent 200-300mb images to work with and having that little bit more power increases efficiency. Also, rendering videos or 3d no longer put my machine out of use for hours on end.
2) iPad Pro - I use this for illustration work using Procreate. As it is raster based artwork, I work with large dimensions to ensure it is suitable for print. My previous iPad Pro supported far fewer layers at large sizes. This meant I would have to merge/flatter down layers which is destructive and irreversible. If a client then wanted a change (which is often the case with client-based work) it would create more trouble to remove elements from merged layers rather than separate layers.
3) My Apple watch is my main tool for notifications, emails etc. My series 4 apple watch no longer has full day battery life which makes it impractical for use. Is it worth replacing the battery on a 6 year old watch? probably not.
4) Airpods. Didn't say these would need upgrading every few years but imagine they probably will. Not massively impressed with the battery life to begin with so after a couple of years I imagine they will be awful.
