Jenkins upgrade 2.150.1 to most recent upgrade path?

Ouch, thats a bit of a large jump. Its probably not what you want to hear, but generally switch to each LTS one at a time and follow the notes on Jenkins LTS Upgrade Guide

Or if your okay with downtime (likely some breakage), setup a new instance, jump directly to latest version, re-install /all the same plugins, and import all the jobs (copy the jobs directory).