Intel to Intel usually goes pretty well. And there isn't much difference between skylake and coffelake, May I ask what CPU you are switching to, it may be more sensible to pick up an i7-7700k, a little overclock, and call it a day. You are giving up an overclocking board for one that doesn't.
You could try the route of just swapping the board and trying to boot. It can work. You'll probably still need to re-activate windows. Worst case you'll have to call their activation line. It is fully automated and you only have to talk to a live person if it isn't automatically authenticated.
Bit of an extreme example, what with only running 1080p, but:
https://www.gamersnexus.net/images/media/2018/cpus/9700k/intel-i7-9700K-f1-2018-1080p.png
Here you can see the i7-7700k compared to the likes of the i5-9600k and i7-8700k. The field isn't that widespread. (They have other charts you can look at)