I first built a Gentoo install maybe around 2007, and had no problems up until the Grub install (however, I had done kernel compilations before). With Gentoo, the two hardest problems you arrive at _during installation_ are kernel configuration, and grub configuration. The former has now been solved with having great prebuilt kernels, or even just a way to use their configs. The latter may still be an issue, but once you wrap your head around it you'll be fine.
I haven't done a new install in a couple years - it just keeps running as-is, so I don't know about the state of affairs, but I would hardly doubt they got worse! I'm sure it's even easier than before.
A weekend is certainly enough time to build a base Gentoo system, and get enough packages installed to be able to use it for daily work.
If you have any problems I would be happy to help someone with a *ntoo setup! My email is in my profile if you run into any issues :)
I don't remember last time I did an emerge world because of this. It's insane.
Most systems these days have EFI bioses, just create a 512M EFI partition[1] and put your kernel(s)(with a set kernel-command line) to EFI/Boot(bootx64.efi is usually the default being loaded). You don't need a bootloader at all(+you'll get a few s off of your boot time too). Many bioses let you choose a kernel at boot time, so you don't even have to play with efibootmgr[2] if running multiple kernels/OS's.
It gets more tricky if you want LVM root fe(which I'd recommend) - in that case genkernel[3] may make your life a lot easier, but even here you don't require a boot loader.
If you do want a nice(er) boot menu, just copy refind[4] to your EFI partition, configuration takes seconds and you can tune it very - VERY - easily
Also, folks @ #gentoo are very helpful, feel free to give them a visit if you are stuck.
And the last thing I want to add - you don't have to compile your binaries on your nb/slow hw, just setup a binhost[5] and compile your tailored packages on your beefy PC/server@work - you can then share them with your devices via http for example
Ok, last one - if you like elementary os, you can get the same look&feel running on gentoo, although it may take some hacks at this stage
[1] http://wiki.gentoo.org/wiki/EFI_stub_kernel [2] http://linux.die.net/man/8/efibootmgr [3] http://wiki.gentoo.org/wiki/Genkernel [4] http://www.rodsbooks.com/refind/ [5] http://wiki.gentoo.org/wiki/Binary_package_guide
..a buildroot micro-system running other distributions as overlays is also a nice time-waster and only a step away from gentoo(+ with lxc/docker there is a lot of long-hanging fruit to collect)
Arch is awesome, I am not currently using it but have used it before.
Another possibility you could look into is Debian Testing. Debian has the reputation of including "old" packages for the purpose of stability, but the "testing" version of the OS is much more up-to-date, and if you need something even newer, and are feeling adventurous, you can install specific packages from debian-experimental.
My dotfiles repository also contains my gentoo config files: https://github.com/JelteF/dotfiles/tree/master/etc/portage Don't copy paste all of it, but it might be nice to see what a config aquired over a couple of years looks like. And some stuff is just nice to have for a desktop/laptop that you regularly use.
I'd say that there are only two valid non-educational reasons to use Gentoo: getting a stripped down (for security or embedded) system or to alpha-test a lot of the free software ecosystem at the same time (e.g. build all your system out of repositories HEADs, a friend was doing that for a long time).
Whether you'll really want to keep with it in the long run is another question. The level of control is awesome, but it is high maintenance. Expect it to break in interesting and surprising ways during updates.
Oh, and this guide: http://www.gentoo.org/doc/en/gentoo-x86-quickinstall.xml