Heh, yeah i'm pretty satisfied with what i've done so far with the forum (i recently added markdown formatting in addition to bbcode, as markdown is much easier to type). Right now i'm still reading through the Python documentation and an
online course so it might be a while, but perhaps you're right that it'd be worthwhile looking into both. At the very least i can share my thoughts when i start to play with Django some.
I haven't really gotten far enough to really get an idea what i can do with Python/Django, but some stuff, dictionaries in particular, seem like they'd be really useful in a language learning site. Ruby seems more web-oriented than Python, though looking through various (offline) scripts/projects online i see Python pop up more often than Ruby.
And i guess the charm of these (super) high-level languages is that you can get started working on more abstract stuff earlier, the gritty stuff has largely been taken care of by others. For example, i was thinking of writing a simple RSS feed parser as a practice project and saw there's a Python package called 'feedparser' which does pretty much everything for you. It might not be much fun and is probably a lot more overkill than i need, but i guess you can get stuff done more quickly. Though i don't care at all for prepackaged stuff like online forum software that takes away
all the fun...
I've never learned a computer language to a useful state, so i suppose it's about time. Ruby and Python both seem like good choices to start.
And add, that does seem like a pretty good fit for me, or perhaps the "reinventing the wheel syndrome"

For the TIs, i often like to write my own code so that i can release the whole thing in the Public Domain without worrying about other people's "give me credit" clauses and stuff. That and it's just more fun to know what everything does.
EDIT: I also hadn't thought about problems integrating Django/RoR with LAMP as i haven't tried either yet. Hopefully it'll be pretty straightforward.