Ok, just a couple of notes.
If you are using portsnap, it keeps the INDEXes up to date. There is no reason for a seperate make fetchindex.
If you are using portmanager, you do not need to use pkgdb and portsdb, which are part of the portupgrade suite. portmanager does not use pkgdb or portsdb, as it relies on the systems database files, which the ports system keeps up to date.
Lastly, keeping your FreeBSD kernel and world up to date is not difficult. You will need the source tree (/usr/src) which you should install from your disk or a downloaded package, csup to update it, and then to do a buildworld cycle to finish it. A little bit of knolwedge about your system is an advantage. Normally I'd just point you to the handbook chapter, but the handbook is somewhat over-complex.
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