I agree that can score decent used or even new gear off of Amazon/kijiji/EBay and would reccomend that maybe for gloves or a jacket but not for a helmet. You (usually) only get one brain in your life time and that's not a piece of gear I would buy used. Way too many question marks. You need to try them on to see what fits properly. Go to a place like Royal Distributing and get a non-current stock new lid. Brain injuries are not your friend.
Agreed!! Kijiji is also good for people selling used jackets... used gloves carry the risk of stinking to high hell, lol. But a helmet should probably be new-to-you for several reasons:
1 - helmets are designed for 1 crash only.
2 - Helmets are actually designed for 1 impact for the most part, which can be as "small" as a 3ft drop.
3 - Helmets won't necessarily show if they have been dropped off a coffee table, from a handlebar, down carpeted stairs, etc. But WILL be compromised.
4 - FIT, as previously mentioned. Especially since you're new. Talk to an expert who knows how it should fit for you.
New gear shouldn't be that expensive really. I bought some workboots from Walmart for like $25 (I don't recommend it though, while they cover the ankle, they provided no real protection); helmet, jacket, gloves all new from Royal Distributing (again, as previously mentioned, and they have frequent sales) for around $200. Don't worry about getting the best gear right now, but watch for sales, learn what kind of riding you'll be doing, etc. Over time you will accumulate hwat you need and higher quality stuff. I now have a $600 Shoei helmet, $300 name brand mid calf boots (bought almost new for $100 from someone I met in a riding group), $300 3 season textile and armour jacket bought on sale for $190, $100 Icon gloves from Royal and gauntlet style gloves bought used (and rarey used by me due to the stink when they get wet) that I picked up just for shipping from a friend of a friend, $300 Dianese waterproof textile riding pants w/removable liner I picked up on sale from Rider's Choice, with an added discount a friend helped me out with so I paid about $180 after tax. If I had sprung for this gear all brand new right away, I would have paid so much more!
As for insurance, you need to narrow down what kind of bike you will be getting. Maybe 2 or 3 choices. Then use an online calculator, and call around to some major brokers as well as the ones already listed here (for instance, TD used to have amazing rates, but this year they went way up... this is common, an insurer wants to attract more riders so offers good rates, gets lots of new riders, pays lots of claims, raises rates, loses riders, a couple years later will lower rates again) so it changes year to year.
Goodluck!