The thing to keep in mind:
Motorcycling is a lot like boating. You can get yourself a dingy that’ll get you around the bay for pretty cheap, but it doesn’t have much in the way of features, and if a big wave comes along you’re going to drown because you don’t have a life preserver. As with boats, the price range (for bikes and gear) goes from cheap and affordable to mind-bogglingly expensive.

Things I wish they’d told me about the bikes:
250cc is plenty in the beginning. You don’t need more power, and the weight & size that comes along with more is going to make the bike harder to maneuver, harder to pick up, and more likely to fly out from under you when you accidentally gun it too hard at a green light. Whatever you choose for your first bike try and get something as light as possible. 350 lbs should be your target. A 250cc bike won’t have as much torque at the high end but you’ll be able to get up to highway speeds without issue.

Chokes are really annoying. If you can afford it, get something fuel injected.

They will happily overheat on you in stop and go traffic.

Dealing with a manual transmission in stop and go city traffic is annoying, tiring, and starts to hurt after a while.

Some bikes have controls that were simply built for bigger hands. You should be able to hold the clutch in, and still easily manipulate the turn signals. If you can’t, or it requires awkward maneuvering, then find a different bike where you can. There are bikes out there that will fit your hand.

Whatever you start out on, no matter how much you love it, you’re going to want something else in a couple years. Maybe you’ll keep your first bike too, but it’ll take a while of riding before you find what really matters, as opposed to what you think matters. So, find a gear-head to come with you and buy something cheap, used, and reliable.

Each type of bike, and manufacturer, has it’s own community of users, and the way each of they all have dramatically different attitudes with varying levels of tolerance for newbs and people who aren’t just like them. The rule of thumb is that the personality of the users tends to closely resemble the visual personality and marketing style of the bikes they ride. Just like the adage about dog owners resembling their dogs. If being able to find others online, or off, who can help you with your questions is important, make sure you can stand the people who ride the bike you’re considering.

Things I wish they’d told me about the helmets:
When it comes to helmets money just buys you bells and whistles. A $75 helmet is DOT approved helmet is going to keep your roughly as safe as a $700 DOT approved helmet. However, the more you spend the more nice features you get, like lighter weight, better air flow, easily swappable visors, retractable inner sunglasses, build in rear view mirrors, etc., etc.

Riding into the rising or setting sun is a massive pain in the ass with street helmets, even with tinted visors. Off-road / adventure helmets have visors but street helmets typically don’t.  I suspect this is because of the wind resistance that they’d incur at highway speeds.

38 percent of the time a head impacts the ground it will do so along one of the jaws. A full face helmet is non-optional.

You know all the jokes about women and shoes? Well apparently you can replace women with motorcyclists, and shoes with helmets, and be roughly as accurate. I have no clue why.

There’s no getting around the fogging, but some helmets are dramatically better at it than others, and it’s not necessarily a matter of price.

Things I wish they’d told me about the gear:
If you’re going to ride your bike year round you’re going to need two sets of gear: one for the summer, and one for the winter. It is unbelievable how much water can pour into a non-waterproof lace-up boot in one second during a downpour on a motorcycle.

Denim, even “heavy-duty” denim, offers you zero real protection.

If the armor isn’t CE rated it doesn’t count.

Never buy a jacket without CE rated spine protection, or pants without CE rated knee armor.

The higher the denier the more tear resistance the fabric offers as you’re sliding down the road. You really want Kevlar or Superfabric but you probably can’t afford either.

If you’re a really careful shopper, and willing to sacrifice some looks in the name of saving money, and only buying the minimum to keep your covered you will still need to spend, roughly:

• $100 on a helmet
• $100 on pants
• $100 on a jacket
• $100 on boots
• $35 on gloves
• … the same again for winter versions of all of these.

You absolutely need to buy, and use, earplugs.

GPS units designed to withstand the vibrations of a motorcycle, and be exposed to the elements, are crazy expensive.

Like your first bike, whatever gear you start with you’re going to want to replace with something else. Fortunately, you can probably sell the old stuff for a little money on Craigslist. Try lots of stuff on in stores, and start with something well armored and affordable that seems to your liking. Next year you’ll know what you really need in gear.

Things I wish they’d told me about riding in the cold:
No matter how well covered your torso and legs are, the cold wind on an exposed neck is brutally painful.

Heated grips are one of the best, and easiest, and cheapest, possible modifications you can make to your bike.

A plug for a heated vest will offer you massive benefits too.

Things I wish they’d told me about the roads:
Bridges where you drive on square metal gratings may as well be ice.

Things I wish they’d told me about motorcycling:
It is one of the most glorious activities you can do: exhilarating, meditative, beautiful.

It is totally addictive.

What do you wish they’d told you before you started riding?

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I’ll add to this list as I think of things, but in the meantime, you may be interested in reading these other posts of mine:

So you want to ride a motorcycle… and not die.
The financial cost of motorcycle safety.