Thanks for posting all of that, I can see there is a lot of thought that has gone into your application and modifications. And I would tend to agree that on the face of it, the question really comes down to: leaning or not leaning? That's a simple enough message that even a traffic cop would understand
I am certified as a CVSA and DG inspector but in my travels I've never met a sidecar inspector from the MTO... They must exist somewhere.
As for the name and badge, I will respectfully decline to post it in an online forum, but I can always be reached through a PM if necessary. I assure you I am legit. I have been in contact with the forum admin and have given my work location and how to reach me.
I don't believe that there is anyone inside of or directly employed by the MTO, that could be considered an expert/inspector in sidecar setups. It's a fringe vehicle, that is declining in numbers by the decade. You might find one or two in the UK MTO equivalent, still.. but they are going to be ancient and farting dust - once common-place in the UK, sidecars are also increasingly rare on their roads also as compared to previous numbers. The UK does have sidecar certification standards related to fabrication and engineering inspection, that allows a minimum standard of vehicle fitness to be evaluated and certified. Not so in Ontario, and for the rest of Canada, as far as i know.
There are a few 'experts' within the motorcycle industry, that do specialize in professional level sidecar setups - perhaps two in Ontario, another on the West Coast that i am familiar with.
Most sidecar setups are done by the trial and error method of 'attract a few buddies to help out with a case of beer, and hope for the best'. A ride or two on a badly setup sidecar rig, tends to scare a lot of them away after that. The survivors/the stubborn will either throw the sidecar back on kijiji, or find someone else knowledgeable enough in the Dark Arts and Sciences of sidecar setup, in order to correct their tipsy-buddy's misguided mis-alignment and setup attempts.
Sidecar rigs, and the theory of sidecar rig setup is one of the last niche Bastions of fringe DIY vehicle design, experimentation and enthusiast manufacture .. and i expect that is because there are so few of them overall, for the busy-body bureaucrats to be bothered with at the MTO, historically and currently. The automotive equivalence of the DIY spirit was legislated out of existence, eons ago. Too many duff kit-bash homebuilt cars were built, and too many incidents.. and they legally went buh-bye as a result.
My own example may be legally registered as a Suzuki Bandit.. about 1/4 of it truly is, anyway... the rest of it came from/through machine shops, certified welders, sourced specialty parts, engineering research and advice, and lots of hard graft at the work bench over a long period of time. I would just hate to see it all undone unjustly, at the road-side, at the hands of a ticket writing bureaucrat just because it's a motorcycle using a car tire. Your 'MC enforcement guru' would be the one that i would fear the most, having a 'black or white' mind-set, at the road-side.
To lean, or not to lean .. that is a risky question. A sidecar rig, using automotive tires, will still 'lean' like a mofo, if something isn't done pre-emptively to stiffen up the suspension of both sidecar and the motorcycle - it's the nature of the beast when the stock suspension is being over-stressed by the CofG wandering all over the damn wheelbase triangle with acceleration/deceleration/cornering/contents loading - an uninformed cop might interpret that as leaning, when told to be on the lookout for evil dark-siders on leaning motorcycles... My rig has exactly 4" ground clearance at it's lowest point - at the swaybar connecting the sidecar wheel to the rear wheel in order to keep it's beefed up suspension flat in corners. It certainly doesn't lean, or bottom out.