Hey, neat – a topic I can actually contribute to!
First: Gear. Go to NewEnough.com and get a full-faced helmet, armored jacket, armored gloves and boots. I wear armored pants, too, but lots of folks prefer jeans and I can understand that.
Second: First bike? Stay aware from anything with “R” or “RR” in the name. A CBR66RR is NOT a beginner’s bike. It’s a track bike with headlights. On the street, you won’t ever use 50% of the capabilities of that machine. And it makes casual rides much more uncomfortable than they need to be.
Then again, 14k RPM is pretty fun :)
Third: Buy used. Many entry-level bikes haven’t changed much in years and used values are very low. Are you a big guy? That will change what bikes I suggest.
Typical suggestions:
Ninja 250 (the pre '08 styles). Not great for the highway for long commutes.
Ninja 500. Better all-arounder. More power, but very manageable.
Ninja 650. Getting even bigger here, but still manageable.
Suzuki SV650. Great value. Good choice. Naked version has less plastic to break.
Suzuki GSF-500/650. Not a bad choice, but lots of breakable plastic.
If you aren’t dead-set on a sport bike, I’d recommend a dual sport for a first bike, too. Lower power, easy to ride. Check out the KLR650, DR650, or DRZ400.
They get overlooked a lot, but I love Buells. The XB9S, XB9SX or even a XB9R would be a suitable beginner’s bike. Lots of torque and a lot more fun in day-to-day driving situations than an inline-4 600cc bike (which requires felony speeds before the fun starts really happening). Almost zero maintenance, minimal plastic to break and get great gas mileage.
I also think that so-called “Standards” are too often overlooked for a first bike. H-D Sportster 883, Honda Nighthawk, Triumph Bonneville, etc are all great bikes that will be much more sporty than 99% of the cars on the road.
Whatever you get, buy it used. Go into it knowing that you’re going to ride it for 12 months and then get whatever it is that you REALLY want.