I vote for 5.8 std because is well tested and you can be pretty sure it will work in whatever kind of hardware this guy have. Just explain the Xine problem and how to fix it, and is a good chance to talk about how Linux handle packages, how is the development cycle, etc.
FOSS usually provide fixes more quickly than other development models. You don't have to be afraid about installing issues, every os has them. There is a recent thread about the problems of installing XP now, and even the ms soft will not play some files because of codecs missing. Every os needs tweaks after install.
However always there is room for improvement, perhaps we are not being very clear about which upgrades are a must, and the patches repo is not enabled by default in the 5.8 iso.
All distros are having problems on this topic. They solve it recommending making all upgrades available after install. I think, and I agree with many others in the forum on this, is not the proper solution, and can bring more problems than solutions. If I understand well, 5.9 will bring a better handling of upgrades, including the "distro upgrade" option, so we are in the way...