To be fair to Gentoo (which has it's share of problems[0] for sure)... it is still far more organized than older distros (Slackware, etc.) in terms of packaging, automation, currency, cross-compilation, security and community. Also, it supports more platforms and features. For Linux all around, the bar has steadily raised. The complexity of a modern system is staggering, Gentoo is the only platform I know that goes the extra mile to allow you to modify everything without sinking in a swamp of maintenance. Yes, there's a convenience cost - but there's a long term cost to not bothering that other platforms extract from you over time.
Its rolling release nature can make it feel overwhelming if you don't surf the bleeding edge. I ran a Gentoo desktop back in the day and if I didn't `emerge world` once a week or so I'd find myself sinking into that swamp of maintenance that you refer to.
Switched my 68 yeard old mom to Linux five year ago. No complaints since that, except for video (so I upgraded CPU) and printer (cable or port is damaged, switched error handling to «cancel» instead of «pause»).
