1. If I take this to court, what should I do? I will obviously higher someone specializing in this to defend me, however, since she advised me to challenge the ticket, will she appear in court? Since she pulled me, and a bunch of people over due to procrastination anyway, I would expect that she is a slacker.
The first order of business in my mind is that your tone is completely disrespectful to law enforcement. You would expect she is a slacker based on the fact that she was conducting enforcement? Please. You're 19, perhaps it's time to grow up a wee bit? You know nothing of how law enforcement or any police service operates and therefore you're in no position to accuse officers of conducting enforcement to keep up with their 'monthly quotas'.
To answer your question, will she appear in court? Who knows. She is required to show up by her policing agency, but unforeseen circumstances come up all the time. Perhaps that day she'll be sick, or be required in a different court, or will be tied up at a radio call, or this or that. Officers will generally show up to a) not have their tickets thrown out the window, and/or b) to collect the off duty court pay.
Considering you're hiring a paralegal to represent you, your appearance in court isn't mandatory. Your representative will do whatever he/she can to get you the best deal.
2. I don't really care about the demerit points, but what do I have to get it reduced to so that my insurance isn't really impacted? (this will be a pain in the ass since I'm on my <span class="IL_AD" id="IL_AD11">parents</span> secondary). I understand that it's the convictions that affect the insurance, but I mean what do I have to get my convictions reduced to so that insurance will consider it no big deal.
It's the number of convictions that insurance companies are generally concerned about. They don't think 'oh well he has been convicted for six tickets but none of them are a 'big deal' so who cares'. Several 'no big deal' tickets (to use your terminology) is a lot more damaging than one 'medium big deal' tickets (like a disobey stop sign).
No, I am not the chief of Toronto Police.
No, I do not work for Toronto Police...
... it is just a name folks