Unless you have heavy bandwidth or maintenance window constraints I wouldn’t worry too much about patch order.
Generally anything super old has been superseded and won’t apply anyway.
If you haven’t seen it, Windows 7 and Windows 2008r2 have a “Baseline” patch you can apply to bring all your machines up to 2016/05 patch levels see: Time to re-do your Windows 7 and Server 2008r2 Patching Baselines!
After that you can just apply patches normally.
Bill