I had been using a keyword search on my Google Calendar with iFTTT integration so if it said "day off" it would turn on a virtual switch and make weekday morning automations run like the weekend however I still don't always get up or go to bed at the same time so it still wasn't ideal.
Last week I completed setting up and automating a bed presence sensor for my wife and I. It's great as I don't have the alarm arm to night mode until we have both been in bed for 5 minutes, that also turns off all the lights and locks doors. In the morning it disarms 5 minutes after the first person wakes up and turns on a few lights then after we are both up for 5 minutes it opens the bedroom shades.