Here are just some of the things that come to mind.
Compatibility is a big issue that I have found over the years. There doesn't seem to be any up-to-date lists floating around. Sometimes I have found myself digging through forum's old topics just to answer a question. Or maybe I have not been able to locate a good list in my searches. And when it comes to compatibility, we are also talking about Distro orientation too, not just if it is compatible to Linux. And the item may be compatible with all linux Distros, it is just you need to tinker to find out why the Distro did not pick it up. Sometimes I just do not feel like fiddling and tinkering, so I find a Distro that works for me.
Wacom tablets seem to have a good compatibility rating. I have one on my desktop. I like drawing, so I use paint programs, I like piddling and dealing with graphic stuff. I have Photoshop CS3 loaded up with WINE. And of course GIMP. And I do have Krita and Fire Alpaca on my desktop as well. I have Blender loaded up but I do not have time to mess with it. Maybe when I retire.
I use the office program, Libre, a lot.
Printers are a big issue I have yet to resolve. HP seems to be the friendliest to linux. I usually end up with an old outdated printer. They are the easiest to find that linux has the drivers for. As Canon scanners are friendly also. The all-in-one printers are difficult to deal with when it comes to linux. Linux cannot find the scanner, or that has been my experience.
I don't game on my computer.
When picking a Distro it is either hit or miss trying to sort through the clutter. You can have a fully compatible computer, whether it be desktop or laptop. But when it comes to selecting a Distro, you end up trying and trying until you find one that will work with all of your hardware. The disappointment comes in when it isn't the one you wanted.
I also surf the net. Because of this, at some point I, or a user, will need to upgrade to a newer Distro. A Linux rolling release distribution is the best route to go. You will have a long term support with updates, usually five years, using that same install. Point release Distros, you need to do a full install to get the newer release of updates, usually every six months. If you have brought to life older hardware, as I like to do, at some point you will no longer be able to upgrade to a newer Distro release. Why? Because at some point a newer Distro release may have needs for a bigger faster processor, graphics card, require more power, more ram, etc. You can use older hardware to run linux just fine on an older distribution. But going on the net there might be some sites, like this one for example, in which an older browser cannot access. (Going to a lite weight Linux Distros can resolve this issue.)