Upgrade ELK from 6.8.9 to latest stable version

What to consider when upgrading ELK from 6.8.9 to latest stable version?

I understand that I should be doing a rolling upgrade from 6.8.9 to 7.16.3 and from 7.16.3 to 8.x
How can I reindex the existing indices?
I also use custom input filters. Will I be able to use them on latest 8.x version?

The upgrade assistant in Kibana is a great place to start!

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