It's been completely painless for me for years. I've got it set up pretty much exactly as the grandparent described: 50 GB partition mounted at /, 600 GB partition mounted at /home. The graphical installer has made this easy since ~forever.
The only pain I can come up with is that I'm wasting about 20 GB, because the operating system doesn't actually need 50 GB. So maybe not a great solution for people who have to do with Laptop with a non-replaceable 128 GB SSD. But 20 GB is not a big deal to me.
The upside is that I've done clean Ubuntu reinstalls two or maybe three times since then, and my data was a non-issue, just reassign the existing partitions and don't format /home. I'd estimate it takes rather less than the 30 minutes the paines refers to, and I always grin despite myself when Firefox restores the browser window as if nothing had happened.