Well it's been a long road but I think I finally have my playthough almost ready - 99% based on the brilliant C&PD guide (thanks Kelmych :) ) and 1% my additions (eg Point Lookout Reborn, etc).
I had recurring crashes during testing at specific areas which I believe I finally tracked down to my active mod sweet spot being around the 203 mod mark - anything above that and weird things happened.
Of course I haven't fully playtested (that would require a playthrough, which I plan to do next) but it seems I have a stable (or as stable as it can be in a Bethesda world) game nearly ready to go, and on Windows 10 as well :)
Hopefully one of my final questions is around Bash Tags - I know there is no definitive answer, but I am curious about everyone's recommendations - I have set or removed specific Bash Tags where mentioned in the guide, and have also set Bash Tags where indicated by LOOT, but if I run Generate Tags for Wrye Bash (no examples at the moment, I'm writing this at work) I have found in many instances that many more extra tags are listed over and above what LOOT suggests. Is it worth adding these extra tags against mods in my list, or does it really come down to knowing what the tags do and what I would prefer overwritten? I'm relatively happy with how everything looks and works so far, so am I better off just leaving things how they are with the LOOT and guide recommendations and actually just playing the damn game? :)