Hi Mat, I can help you with Q2, not so much on Q1 (still struggling).
Regardless of what anyone tells you, whether it's Microsoft or people like me, Windows 10 is completely riddled with problems from the initial installation, to an through the latest build. Those on the inside that suggest otherwise are lying (more like ignoring). Those on the outside are only kidding themselves...it's not a matter of if, but when. I experienced minor nuisances with each and every build since the first release...and it gets worse (further aggravating) with each and every release.
The only positive experience I've had on the 10 platform is when using, albeit in a test environment only, the LTSB versions of Windows 10 (A bit of humor inserted here). I'm convinced that (a) the recent shake up at Microsoft will help to alleviate the pain/struggle, but (b) we're stuck with the OS as a service mindset until someone at Microsoft steers the company back from which they came.
Anyway, per this fact sheet, you should be OK with 1809 (beyond the posted end date):
https://support.microsoft.com/en-us/help/13853/windows-lifecycle-fact-sheet
Good luck.