Cannot recommend container approach enough. The learning curve isn't too bad, initially it can be daunting but best way is to jump straight in and try it.
Few things I recommend:
- Portainer, a very nice container management webapp
- Use compose /stack from day 1, or at least try it before you get carried away with too many containers. Take a copy and save somewhere and build up your catalogue of containers/configs.
- Volumes, make sure they are persistent.
- Backup your docker config folders, especially if using development branches.
- Spend a day/weekend playing with setup, expecting to throw away and start again. Sounds bad but it's not. If you use compose/stacks you can spin up in seconds.