In what way the auto update would help? Code42 has done some undocumented modifications on how headless server works. In this case, wasn't just about updating CP, but release a 4.3 version of both CP and CP-Desktop.
Other example is NZBget; the author made some serious changes on how the program is installed. It took some time to figure out and modify the code accordingly.
With the exception of a few guys that have goodwill and submit some changes to the GitHub repo or send debug data, most of users just take things, never giving anything in return. Sacretagent sent me some PM, a guy named Datapotomus submitted a PR (it wasn't just about version update, so I didn't merged it, but thanks!).... Thanks a lot guys, this kind of thing helps a lot!
For you, opentoe, good riddance with your VM solution; I'm sure it works just fine. Thanks a lot for your input.