Transman VS Insurance Company?

So I'm quickly approaching the point where the company that currently covers all my transition needs can give me the bump off if I don't do something. I'll be turning 21 in a mere two months and unless I give them sufficient proof that I have a pre-existing condition I'll be on my own for the cost of testosterone and visits to my counselor (aka my ticket to the head of the line for all transition resources)...

Has anyone ever gone to their insurance company with G.I.D as a reason for them to continue coverage (Canada or Ontario in particular)? I'm technically on the plan still as a dependent of my father (it's his work coverage) which is why they boot you at 21 if you aren't in school full time (and I just graduated)... or at 25 if you are deemed worthy.

I keep thinking I would only qualify if I had a really serious condition that required an excessive amount of care.... I don't think that of transitioning and feel like I'd be cheating to use G.I.D (and that I'd be buying into the "oh, I am ill" BS). I think it's meant for adult children who have conditions where they cannot care for themselves... like physical or mental disabilities... Would being trans keep me covered until I am 25?

Also... would playing my "G.I.D card" now mess me up for personal insurance coverage later on in life? Would I be shooting myself in the foot?

A million thanks for any information, suggestions, or stories on how you managed to beat the system (or even how the system caught you) while transitioning.

A few hundred laughs in your face to the trolls, haters, and people who feel the need to tell me that being trans is "wrong".