I started a real update to the port but was unable to complete it quickly. I have more pressing coding tasks and can’t spend the time now to complete the port.
My short term solution is to just use ruby gems to update itself (assuming you already have gem installed, if not see below).
sudo gem update --system
Then, if you want to, update some installed gems (like rails -> 2.0.2)
sudo gem update rails
I updated my systems which run my ruby-1.8.6p110 port. However it should work with the stock ruby and gem which you can install via OpenBSD ports:
sudo su # setenv PKG_PATH "ftp://ftp2.usa.openbsd.org/pub/OpenBSD/4.2/packages/i386" export PKG_PATH="ftp://ftp2.usa.openbsd.org/pub/OpenBSD/4.2/packages/i386" pkg_add ruby ruby-gems ruby-iconv gem update --system
If anyone has a pointer to a completed native port, please let me know.