I have updated online several time over the past few years. Do portage first; then GCC and the basic system utilities (glibc, make, binutils, etc...) If you need a new kernel, make it and then reboot. I would then do OpenRC and the rest of the development chain. Finally, anything else.
I have also done the chroot install and replace. The main complications it to make sure that configurations for your system (passwd/group and others from /etc) get transferred over before you get too far into the installation into the chroot. Good luck. You may email me if you want more details. -- Gregory "Wolfe" Woodbury redwo...@gmail.com
