Typically issues that you will more then likely run into are going to be driver related, either with your your production hardware (printer etc) or with your individual computer component hardware (video card etc).
Rather or not any of your components still have support will probably determine if you will ever get Win 10 support. Part of the problem with trying to be "bleeding edge" with computers. There will be a while of playing catch up. Being a heavy Fedora user, that is something I know all too well at times.
However, due to that, I usually suggest keeping the "bleeding edge" stuff away from production computers unless you have the time/inclination/knowledge to work through the "pains" to get it going.
there is NOTHING wrong with windows 10. I upgraded from win7 and never had a single problem. Not with apps nor games.
Your mileage may very. I've known some people that have very expensive digitizing software that made the move to Win 10 and it wasn't compatible (nor was the company supporting that program on Win 10, which the company gave more then fair warning about before Win 10 went live) and broke their install.
That kind of stuff you run the risk on no matter what OS you are upgrading to. When mom went from Win 7 to Win 8, it broke her Ps CS6 install and broke Corel DRAW install. It happens. I think a lot of variables come into play when upgrading an older computer that people don't realize.
Having said that, the one thing that I do find wrong with Win 10 is that it is very invasive, even if some things are overblown by tinfoil hatters, an OS shouldn't be that invasive. Certainly some things shouldn't be enabled by default and not being able to turn everything off, I don't like have incoming/outgoing communications that I can't control. It doesn't matter if the OS is modern, appealing and/or easy to navigate compared to previous iterations, it shouldn't be invasive. But that's just me.