Upgrading from 0.41 to 0.6x In Future

Currently, I’m running Home Assistant 0.41 and haven’t seen a need to upgrade except for breaking changes. I will be away from Home Assistant from 9 to 12 months starting before August, so here’s my question: Has anyone done a backup of Home Assistant configuration and started fresh? Meaning, has anyone upgraded Home Assistant that’s about 10+ versions later (such as 0.35 to 0.45) in the past? What about upgrading 20 versions later?

The reason why I ask this is I will be going to World Services for the Blind and go through training for Desktop Support Technician, which includes certifications such as A+, Security+, and Network+. And while staying in the dorm, I will be missing home automation, but then I’d be busy studying to get certified. Dorms do not have smart home technology, so it makes sense to leave Home Assistant running at home.