django 2.x is not lts, next LTS version is 2.2, as said before.
-- That said, I'd break this into three chunks:
migrate 1.8 to 1.11
migrate 2.7 to 3.6 (or 3.7)
migrate 1.11 to 2.1 or 2.2, depending on the timing. 2.2 will be out in April 2019, which is seven months from now.
I would separate framework update from python version update to minimize bugs and simplify the upgrade process.
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