The best way to go is to sign up to take a course with a local motorcycle school. You are looking at about $600 or so. Depending on the school, some offer daytime, week-long evening, or weekend courses. If you are out of shape, not particularly athletic, need more time to learn new things, or are past middle age, I would definitely recommend a week-long course. This allows your body time to recover and your mind time to absorb and digest the lessons, plus you have the advantage of a little unstructured practise time if you get there early. All schools will require you to wear a minimum level of protective gear, although some will provide it if required, either for free or for a minimal extra cost.
If you are planning to buy gear before your class, I recommend you spend as little as possible on gear with maximum protection. You may find out that riding is not for you and you don’t want to be stuck with a bunch of expensive gear. You can buy second-hand gear on Kijiji for significant savings, but it may take some effort to find what you’re after. Keep in mind that it is recommended to replace helmets after five years regardless of actual use, although I take that with a grain of salt. You can also buy new gear that may not have a bunch of high-tech features or the latest graphics, but will have excellent protective features, such as elbow/shoulder/back/knee/hip armour and tough fabric in the right places. There is little difference in protection between an inexpensive helmet and a top-end helmet if they have the same safety endorsement, such as Snell or US DOT. Your are paying more for things like lighter materials, higher quality lenses, sound level, comfort, and graphics.
Unless you are huge, I would not buy a first bike larger than 550cc, and I would buy a second-hand bike that already has a scratch or two on it. 250-350cc might have trouble maintaining highway speed against a strong wind or a steep grade, but will otherwise be fine for keeping up with normal traffic. My first bike, at the time nine years old and 400cc, could out-accelerate most cars from a stop light.
I was 39 when I finally got the green light from the wifey to start riding…I started on a 500cc twin. It was a great bike. I completely agree with Gryphon Rider, a course is the best answer. Even better than getting a buddy to show you how. It avoids picking up bad habits from the buddy (even one of us would probably show you bad habits, so take the course…they are worth every penny!) I found the riding course made me a better, more aware driver when I’m in my car/truck.
I would also urge you to hold off buying a bike until you take a course. They usually have a few different types of bikes and you never know which type you like until you are in the saddle for a while. Take the opportunity to sample all of the different bikes available.
It is a lot of fun, getting into the community and starting to ride…I don’t ride nearly as much as I would like, but that should change this year…less change in 2015 for me!