Hi,
IMHO half of the points you raise are subjective, especially the remarks about file and app naming (Windows is as guilty of this). Half the point of Linux is that you CAN look under the bonnet and take full control, so if you don't like an OS that will allow you to do that then Linux will never really satisfy you. Having that power and control over your PC is half the point of having FOSS on there to begin with
I use F8 myself, and it's a great OS. However for what you're after it will probably be too hands on. You'd have to manually set up the third party repos and add multimedia support for example.
When you ask about a proper application installer 'like Windows has', are you referring to Windows' .exe format? Linux loads software from the repos as easily as (and much MORE seamlessly than) Windows. But you probably already knew that.
Having read your post twice, if you're going to try a flavour of Linux and want it to "just work" I'd suggest you check out Linux Mint. It has all the multimedia (codecs, flash, JRE etc) set up out of the box, and "just works". As it's based on Ubuntu, it has graphical tools for just about every requirement, so no need to touch the CLI if you don't want to (though you're missing out on a great tool). Further, Mint is able (just like Debian, Ubuntu etc) to install from .deb files downloaded from the internet. Basically they're the same as Windows .exe files in that you download them, double click and click "OK" to install and you're away.
Mint also has Mint Update and a Software Portal for software packages which is in addition to the standard OS repos (it holds customised .deb files, which Mint calls .mint files - examples include Amarok, Gnome Games, etc).
Fedora, or indeed just about any distro these days, is easy to use if you're willing to sit down and do a little learning. Or rather, as a Windows user, some "un-learning". I tend to find that folks with little PC experience (even of Windows) adapt to Linux quicker because they don't have to "un-learn" their Windows stuff first. JMHO.
Again, if you want an OOTB experience and don't want to use the CLI or utilise the full power of your box, a basic install of Mint will suit you better. Whatever you try, do try your best to drop the preconceptions and expectations - you'll have a better experience for it.
All the best, and good luck whatever you choose.
EDIT - BTW, Linux has far superior management to Windows. So no, you won't need to worry about detritus being left all over your hard drive, and there is no 'registry' to get clogged up. Just in the same way that Linux doesn't need defragging, as the way it utilises your drive means all files are by their nature contiguous (unless, maybe, you have less than 5% or 10% free space remaining).
