To me P2P is the obvious answer to the (especially free) software distribution problem. Sign the binaries, and let the users help you. You can even run Opentracker [1] on a cheap server for more independence. Ubuntu is doing this.
But I'm aware that doesn't work for everyone, since most people (especially Joe User) are using either Windows or Mac OS. For Windows, Ninite covers a decent range of basic freeware and open source software, and Chocolatey covers a lot more but is less user-friendly. For Macs (and I shouldn't have to tell anyone here about this) there is the excellent Homebrew project.
Back to the Windows arena, maybe Microsoft's new package management system will be a boon for power users and those seeking good freeware for their computer without having to worry about tagalong malware.
I know many people who had absolutely no trouble downloading various things - including software - from all the P2P networks that flourished around 10 years ago. Not only torrents, but eMule, Kazaa, Limewire, etc.
They also happened to easily infect themselves with various malware by doing that, but I'd consider it more evidence of how "non-geek" they were.
(But all in all, despite the risks, I definitely prefer and miss that era of open filesharing compared to the closed proprietary walled gardens that have replaced it.)