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All three environments (dev: Vagrant, prod: AWS, CI: Travis) should be updated in sync. We may have to replace Travis with another CI system but I don't think it's necessary to have a separate issue for that.
Currently used version 16.04 LTS has end of life date April 2021
Ubuntu 18.04 LTS has end of life date April 2023
https://wiki.ubuntu.com/Releases
Python 3.5 (included in Ubuntu 16.04 LTS) end-of-life is 2020-09-13
Ubuntu 18.04 LTS comes with Python 3.6
https://devguide.python.org/#status-of-python-branches
Considerations:
Resources:
Requires: upgrade to Django 1.11 (#2572)
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