My current school has pretty limited course selection and extracurriculars. Its not super limited, and certainly nowhere near the worst of public schools, but it’s not what I want from my secondary school education. I also really want the thorough college prep that these schools can give for me!
I’ll also be applying to IAA for Creative Writing, so It’s also about passion in a lot of regards. My current school has zero writing clubs and very, VERY few opportunities 
yes def
if you’re interested in new england area, look into governor’s, lawrence, & kent (although kent is on the tougher side) i also need FA and i’m not an athlete but it’s also important that parents on websites like CC aren’t actually the AO’s reading your app— that’s what you gotta focus on impressing
it’s all about your mindset, so do everything in your power to build a very specific image for yourself (think: these niche activities, service work, etc) and apply to as many schools as able to that you think you’ll fit in at. odds are, you may be the person that they need to fill in a certain gap
definitely don’t get too delusional because i’ve fallen victim to this lol but i believe in you!! do not let people stress you out because that will only psych you into making a worse application.
Hopefully by the time I’m applying I’ll have one a sliver or gold key at hopefully national but probs regional level at the scholastic arts and writing awards, which’ll really help me sell my image. I’ve looked into all of the BS’s you mentioned and honestly I might just try throwing myself at all the schools I like ahah. It’ll be a busy year! Might start writing applications now, just to give me a taste/give me some time.
one think that’s super important is to drill it into your head that awards are not guaranteed. i know it’s easy but try to erase the “hopefully i’ll have xyz…” because at the moment you don’t and there’s always a chance that you won’t so you need to think about how you can best utilize what you currently have
if you can afford app fees. GO FOR IT!!! if you like the school and would go there applying can only help you (note: if a school asks during an interview which schools you applied to, probably don’t list all of them)
doing applications insanely ahead of time is also kinda pointless because a lot of growth happens between 9th and 10th grade, so i would recommend maybe coming up with ideas for broader essay prompts maybe a few months out from now
if you need any further advice PM me because i love yapping 
There’s a lot of info on this site about reclassing, and it’s a really personal decision. Lots of student do it. If they’re on the younger side, it gives them a chance to mature (which can matter more in a residential community). If they’re athletes, they get another year to get bigger and stronger and improve their skills. It gives them a chance to learn the ropes before junior year, which gets a lot of scrutiny in the college application process. And those who reclass, rarely repeat material because BS are set up to provide lots of accelerated and advanced material. This isn’t like going to the public school a town over to repeat a grade! But plenty of kids don’t reclass either.
My advice? Ask about it in your interviews to find out if they recommend it, if you can ask to be considered for 10th and 11th, or if you need to specify one. Many schools are super concerned about 11th grade admits simply because there is so much at stake, so it’d be good to do your research and pick the right path for you at each school – you’d likely get different answers at different schools.
As for reaching out to teachers, etc… You are best off doing this through your AO. You can ask in an interview if they could connect you with students or advisors for the literary magazine, paper, etc. to learn more. But do everyone a favor and make sure you’ve read everything online, etc. first. Your interest needs to be genuine and informed. If the AO connects you, it’s fine. If not, it will probably be of little to no help and could even backfire. These folks are busy and may not have any input in admissions decisions.
It’s good that you’re willing to expand your list – there are SO many great schools out there, and you only need one! Schools select students they feel can bring something to their community and who they think will thrive there. As an applicant, it’s often hard to assess both these things, but you sound like you’d be a great addition for some schools. Definitely look at schools that are strong in the arts – nobody wants to take a student whose strengths they cannot nurture, nor should you settle on that front. And figure out how you can jump in right away, whether with MUN or something similar. The schools will be assessing how quickly you’ll get up to speed, not just in the classroom.
Welcome to CC! Excited to follow your journey!
As others have suggested , first review the websites of the schools you are interested in and you can also find additional information on CC threads. Now would not be a good time to contact the AOs since they will be in committee and planning on selecting the next class. Subsequently they have spring break and revisits. There will be time in May and some have visits in summer when you check them out as well
Those are REALLY hard schools to get into. I would broaden your choices for schools (look in the hidden gem thread) if you really want to go to boarding/private school.