1. Have been using USB docks corporately for a while; usually use Targus, some include power to charge your laptop if desired, especially if the model you are looking at supports USB-C, though these are pricier. Have deployed probably about 150 targus docks in the last 5 years, have had probably 10 in total break so far (primarily age related, ports wear etc). I consider that reasonable given wear and tear relative to other docks.
2. Win 10 Pro has a couple features you won't use based on what you're saying you use it for. Not worth an extra expense if not using corporately IMO. On the other hand to upgrade is not cheap, so if it's only $20 more why not . . .

I agree the L series can be a bit on the cheaper side, if you can get an X series or T series you'll likely get some better longevity from the system. I guess it depends on how long you think you'll keep it for.