migrate from 1.x to 2.4, then use the migration tool, reindex and upgrade to 5.x,
create a new server, install ES5 there and just reindex everything there directly from our Django app, we have tasks for creating indexes and indexing all the records too.
Is there any specific reason to use the first option?
Not really. Given the gap I would definitely suggest deploying a new cluster and then reindexing, you will be able to take advantage of all the awesome new data structures and give your mappings a refresh
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