Rain
Beepster
You can Wiki for all the timelines and where everything falls into place as far as series and specific eps and there is that alpha site that keeps even more meticulous records on it all.
but I swear... I'm a musician... not a dork... DAMMIT!
I'm addicted to Memory Alpha (the Star Trek wiki) as well as all the rest of that stuff. :)
I do consider myself a Trekkie in some ways - though I'm not an outcast unless by choice, I don't collect toys, I don't own a Federation shirt and you wouldn't catch me within a ten miles radius of a ST convention.
I do drool over some of those Enterprise models, but who doesn't? :P
That being said, DS9 is the first series which made me want to check out the books. The series had ups and downs - one of the last episodes, Extreme Measure, was particularly unbearable - but it's a universe with much potential.
To be honest I probably never would have been motivated to watch all the ST stuff if I didn't need to do hours of physio a day but it is indeed a very interesting universe especially after spending some time learning about basic astronomy and astro physics. When I was kid ST TNG was new and seemingly on TV all the time but I always ended up falling asleep because I didn't really understand it.
As far as the books... I am intrigued because it's all very addictive as far as wanting to figure out what's what and filling in the blanks (even the non canon stuff) but I can't hold books while stretching and flopping about so any reading that gets done is strictly technical manuals and now with the intertubes I don't even really bother with paper anymore anyway.
I just remembered though I haven't watched the reboots yet but I hear they broke a lot of the original mythology. Even Enterprise had some kind of dumb things that didn't make sense in a historical concept but I liked that in the last season they put the effort into explaining some discrepancies (like the Klingon virus but if you haven't seen that stuff I won't spoil it). They should have spent more time working on fleshing out the history as a prequel instead of going all weird with species and wars never mentioned before.
Toys, shirts and other dealibobs are simply things that I don't get into to. I'd rather spend the money/apartment space on useful stuff like music/computer gack. I did have a pretty cool Star Wars collection as kid.
I'll probably rewatch the original series again soon because I've only been through those once. Much lulz to be had with those.
Cheers.