Replies:

1) RPM/SRPMs are a huge headache sometimes, solve this solve that. I almost feel like I am back in Calculus in college.
2) Being able to divert easily from the main portage tree is a huge benefit when your Gentoo machines are production servers and you need to insure the stability of your packages and builds (example, apache, mysql, php, postfix, openssh, openssl packages). Also diverting from the main portage tree and creating your own ebuilds on production servers that are internet accessible is very handy in making those packages I listed earlier more secure and trust worthy because you can get the official source from the distributor yourself.
3) Gentoo has a very lively crowd when it comes to documentation, howtos, faqs, and bug listings. Their forums and gentoo-wiki.org are goldmines when it comes to setting something up quickly and there are plenty of diverse topics on systems administration out there so 10 day installs really shouldn't happen unless you have some highly experimental hardware you are working with.
4) You have two options, RTFM or install Windows and click the next button until something works.