At first, I would do your step 1. I would check for any other errors in Django 1.8, and then proceed with updating to 1.9 -> 1.10 -> 1.11 -> 2.0. You are probably going to find other issues that need to be resolved in those upgrades. Ultimately, you will probably have to do step 3. I wouldn’t do step 2 since you’ll be updating all of your templates. If you are going to update all your templates, you might as well just do step 3.
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The only change in escaping behaviour in 1.9 was around the output of simple tags, see https://docs.djangoproject.com/en/2.0/releases/1.9/#simple-tag-now-wraps-tag-output-in-conditional-escape - this is a very minor change which can be easily fixed within the tags themselves.
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DR.