Frankly, most of the whistles and bells in later versions won't help me any, and in my profession, I don't want connectivity beyond what I have now. Forget the cloud, neither I nor my clients want all that data out there where it can be hacked.
Currently, windows keeps updating XP, and until I can't get the job done with it, I'll be using it.
It is amazing how much has changed, but most of that is aimed at the send video/facebook/piddling on the web crowd and not just working (at least not the kind of work I do), and really isn't useful to me. I prefer the more boilerplate menus and formats because they are easier to work with when you are on your eighth straight twelve to fourteen hour day with an average of four hours of sleep.
Much of what may have to be converted to carry it over is archived on thumb drives and large backup drives already. As for the machines, internal hard drives are cloned and replaced every two years, (MTBF in my case proved to be about 2 yrs, eight months, and I can do without that stress.)
I have replaced cooling fans, drives, displays, inverter boards, power boards, memory, batteries, AC adapters, and even hinges, ('board' replacement level repair isn't hard--but anyone who can fix the boards has my respect) and the machines keep on going--and the parts are affordable because there are enough machines out there being cannibalized to keep mine up.
It's better to upgrade to a newer system while both systems are working. I'm sure you understand the value of this, being able to get use to the new system, while still using the old system.
True, and eventually I will make the jump, but that won't get the job done tomorrow.
I'm waiting for a system that gets the reviews XP did, and by then it'll be a quantum leap.
I'll have to reinvent the wheel, but it'll be on a system which people will want to stick with as much as XP, so it will be around another decade or more--by then, I'll likely be retired or dead, so beyond that it won't matter.