I looked into a dedicated managed server and it did not give me the flexibility I wanted. Fewer resource limits, but the lack of admin rights is about as bad as shared hosting… Can you imagine having to contact support when you want to upgrade an extension or something? Maybe if you have no sysadmin skills that would be a good choice. I can easily run a server myself and I don’t want support staff at some random host administrating my server for me at all. I think I tried a managed dedicated server for about two weeks before switching to unmanaged.
I did what I’m describing very successfully 10 years ago and I had a very good reasons to make these decisions at the time.
I mentioned python because I ended up re-writing everything in python two or three years later. You’re right that it’s not related to this, other than that trying to run a python app under shared hosting was really difficult.
I moved to a unmanaged VM (this was 2008, first Slicehost and then Linode) since I’d been using Linux as my main home OS for 10 years anyway.