linux-window-session-manager VS super-productivity

I doubt I'll have any insights to solve the actual problem you're having, but I and others may have suggestions for waking it less painful to restart your workstation. For example, I have a script I run for to restore my windows for my day job. What are you running your containers on? Could starting all of those up be easily scripted? As for window restoration, I use lwsm. It's not perfect out of the box, I had to add an application definition or two, but now it's what allows me to launch my work windows in just a few moments

This might work for you https://github.com/johannesjo/linux-window-session-manager I have not tried it.

I implemented a workaround by installing the npm package linux-window-session-manager and then using crontab to launch it on boot. It doesn't auto-save the session on shutdown though. I have to do it manually.

SuperProductivity ( https://super-productivity.com/ ) cross-platform and feature-rich, been using it for a year now.

https://app.super-productivity.com/#/tag/TODAY/tasks This cannot do 2 and 3 by itself, but it can integrate to many calendar services and achieve 2 and 3 through it. Manual here https://super-productivity.com/

Super Productivity (version 20.0): Free to do list & time tracker for programmers & designers

I had a lot of luck with super-productivity for a while. I liked that I could store the data on my own webdav server and have it persist across all my devices, while being free and optionally self-hosted, but there is a learning curve when getting it set up.

If data privacy is a concern for you, you might want to consider a FOSS alternative. Condution is a good option that is available on almost all platforms including MacOS and Android. I haven't personally tried it but Super Productivity is also another option.