Presumably you have Time Machine running and backing your entire system up on a regular basis - You may want to 'clone' your system as-is to another external drive using Superduper or Carbon copy cloner.
Once you're certain everything is backed-up then jump right to Sierra. Yes its got the 'flat-look' but most of the bugs are dealt with now as its at 10.12.5 You have an SSD so you may not find the lack of RAM such an issue as it would be if you had a HDD.
Try Sierra for at least a day, giving it time to settle down with Spotlight indexing etc. No point in going for anything less if you're upgrading now.
Unlikely but if you find it slow, you can easily restore your backup. The longer you leave it the harder it is to go back as you'll need to keep track of documents etc.
If you're also an iPhone user, take care not to opt for the iCloud Drive until you're happy with the new OS, you may mess-up the ability to go back to iPhoto sync from Lion.