And there are worse scenarios than python upgrades. What happens if your processor or your OS reaches end of life? Do you keep running the whole stack on Windows XP without security patches until the last bit is ready?
No technique or tool will fix your organisation.
That sounds to me like you are complementing the downsides of running a monolith with the downsides of operating a distributed system, without any noticeable upside.
I wouldn’t run a system where the two servers call one another.
This is a technique for reducing risk via toggles at the load balancer. The reduction is achieved by making it possible to deploy smaller changes to users, and by reducing the latency of rollback.
These are only useful if you have the ability to introspect the system state in production and confirm whether a new version is working correctly.
It sounds like you're referring to blue/green deployments without using it's name, for some reason, and while failing to present any case of why a monolith provides an advantage. You're just showing downsides without any upside as a tradeoff.
I mean, with microservices you can also do blue/green deployments, and they are not all-in like monoliths. Each deployment only covers a subset of features that can gradually be rolled in and out with the only risk of causing partial failures.
You can do all these things either way. The question is which way suits your tools and organisational structure.