I agree with @anxiousenior1, especially since Amherst focuses so much on diversity for an elite school. I do think you should transfer if it's not the right place for you, but your comment about privileged backgrounds makes me think you've only interacted with a subset of Amherst's population. Almost all of my friends, for example, are first-generation or Questbridge scholars. It might be that your specific interests or hobbies are causing you to meet people from privileged backgrounds; if this is the case, you will probably have the same problem at other schools.
Transferring can be very competitive, but I think you will have a good shot if you aim at schools a little less selective than Amherst/Ivies.
Check what you feel most describes you. From what you've said, that would either be Alaska Native or Alaska Native/Asian. Just be yourself, and don't worry too much about the impact of your background on college admissions.
Amherst is the obvious choice here for your interests: liberal arts college, open curriculum, college town setting, great English department. It's a reach for everyone, but you're competitive from what you've told us so far.
I don't understand how you are a special case. Your ECs look fine to me. You have a lot of community service and a long history of competitive chess. I can't say if it will be "enough" for UVA, but considering you are in state and your stats are okay, you may as well apply early action.
I also don't get what you mean by "setting the bar low." UVA is one of the top ranked public schools in the country, and W&M is very highly ranked as well. You are lucky to live in a state with good in-state options.