In my experience, the main hassle has been Gentoo maintainers of some packages who, for years, stubbornly refused to accept minor patches (and they were getting

In my experience, the main hassle has been Gentoo maintainers of some packages who, for years, stubbornly refused to accept minor patches (and they were getting smaller as compatibility improved) for LibreSSL support (because always talking about risks has made people frightened about touching anything which relates to 'security', they prefer to shift responsibility on upstream, and you find the same kind of people upstream, afraid of putting two lines of #ifdef in their 500,000 lines bug-ridden project), thus users had to maintain their external overlays, and update them again each time a new version of the package appeared (if you consider that nowadays some projects publish releases every few weeks and that Gentoo is a rolling release...). That's a small part of the reasons I don't use Gentoo on my main box any more, I got tired on fighting with maintainers who will spend their time writing 50 messages to deny people's requests and yet refuse a 5 lines patch pretending it is too much work or they can't "analyse" it. That behaviour is unfortunately not specific to Gentoo maintainers, of course. So now, I build my software myself, I make or take patches myself: anyway that's how it always ended, having to do the work oneself, but at least it saves the time wasted arguing with maintainers and waiting for them to finally commit the ridiculously small needed patch for months to no avail, and it saves my nerves too. And don't get me started about "packages not being tested against LibreSSL": it is not like they were being tested against anything; the number of times users have complained that some package was pulling a stream of unneeded dependencies, or conversely was not pulling an actually needed one... because the maintainer had just gone "oh, it worked on my machine" where all dependencies were pre-installed. I am talking about major stuff like web-browsers or toolkits, not some little rarely used piece of software.