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You can try my python-mls package for the 3rd. It enables multi-line commands in (i)Python and provides several other features, including pyhist files tied to the shell buffer name (it needs to store multi-line history specially).
I went from an old config rich setups from before lsp's to lsp-mode ones etc... Right now I would say that eglot + pylsp gives you the best experience, you can use pyenv and pyvenv mode to manage your virtual environments. Now that treesitter is also being used you can try out https://github.com/mickeynp/combobulate