Welcome, O6, you have been infected.
Actually, I'd support Gomess and Prowl's advocacy of Kabuto and W respectively. Both are good series.
In fact, any of the "Heisei" era Rider shows which started in 2000 are probably a good starting point. Most of them are standalone series which you can pick up without confusion over continuity. The only exception is Decade, which was a tribute/fanwank series that made references to ALL the past Riders in some form or other.
Also, the recency of Heisei Riders might make for easier viewing than the old 1970s/1980s fare. Of course, the fact that these are, first and foremost, elaborate commercials for kids' toys - more blatantly so than the original batch of Rider shows - means that you shouldn't be surprised to find some facepalm moments and major plotholes. Even the best of the Heisei Rider shows have such flaws.
You can find a good number of them streamed from dramacrazy.net. Just look under "K".
Alternatively, TvNihon has subbed most (if not all, by now) of the Heisei Rider series and have them all up for Torrent on their website.
If you're gonna go old school, then I -would- recommend starting with the first Rider, Ichigo. Not only because that one started the whole franchise, but because most, if not all, of the older "Shouwa" era series are chronologically linked. These series are harder to find though, and Gomess' torrent links are the only leads I have.
Ohy and before I forget, there was a kind of remake of Ichigo as a feature movie a few years back called "Kamen Rider - The First". That one might be easier to find, and, despite being a fairly recent production, it captured a lot of the spirit, drama and tragedy that made the original so awesome.
Just to avoid multiple posting:
Gomess wrote: Currently going through Ryuuki, enjoying it more than I thought I would. Never knew it had a whole Highlander thing goin' on, and I like the stupidly large cast of Riders (shame it became the norm around that time).
Ryuki had some good things going for it. As unexpected as it was, the writers did succeed in using the ludicrous "hunt monsters in another world" premise to pump up the drama quotient. I did mention in my first post here that Ryuki was a good contender for being one of my favourite Heisei series. It's just that I generally didn't like the underlying monster card gimmick, and most of the characters were just too one-dimensional.
It was nice at the time to see a whole bunch of riders in one show, but on the other hand, I blame that as the main obstacle against having enough room to develop any one character decently.
Incidentally, that was one of my gripes with Kabuto as well. I think it's a good show overall, but characters like Drake, Kickhopper and Punchhopper were pretty much just there to inject more toys into the line.