There are 3 companies that will insure SS bikes in Ontario
State Farm - I believe they have an age requirement of 25, and 5+ years of driving experience since G1. If the age isn't a requirement its when the 'affordable' rates would kick in. Pay all at once, or monthly
TD/MM - The big discounts don't start until your 30 iirc. Pay all at once or 7 payments over the spring/summer months
Nordic/Facility - Most expensive of the 3, no requirements for insurance, one lump sum payment option.
Contact Information
State Farm
Anna Raeli
Address: 2201 King Rd #2, King City, ON L7B 1G2
Phone: (905) 833-2662
Hours: Wednesday hours 9:00 am–6:00 pm
TD/MM
Live Phone Assistance: 1-888-791-5346
Monday to Friday 8:00am to 8:00pm. Saturday 9:00am to 4:00pm
Nordic/ Facility
You will need to go through a broker, which you have already done (JRD)
Jevco/Intact do not insure SS bikes any longer, nor does Riders Plus so neither of those are options for you.
I believe I have covered all of the options which are available to you. You wanted peoples personal experiences with the insurance companies, so heres mine. I'm 29, 10+ years of driving experience, M2 since Oct. 2012. With State Farm I pay 1368 a year (114/month). My quote from TD was $1800/year (they told me to try them again when I was 30 for more competitive rates), and from Nordic/Facility it was $2300/year.
Does that information help you at all? No it doesn't, because you do not meet the same requirements for the same rates as I do. Most users on here that ride SS bikes qualify for either State Farms good rates, or TD/MM. The ones that seem to be in the same age bracket as you are either on smaller bikes, or asked the exact same question as you did, but when they got their quotes and found out there is no magical way to pay ~1000-2000 for coverage on an SS bike when you are younger than 25, the majority don't seem to stick around.