First, you accidentally shrank the last part. Can you unshrink it for everyone else, who can't copy and paste into word and resize?
Your questions.
Insurance - Do the math. Figure out as best you can what you'd have to pay for both plans. Include premiums, copays, coinsurance, etc. My guess is that there's going to be a plan that has lower costs for you. Make sure it has your doctors in network, then go with it.
Savings - After the emergency fund, I'd recommend a tIRA. The problem with 529s is that you get locked into using it for education. You have more options with other types of accounts.
Writing - Do the best you can. It's very hard to make a living that way. If you want to be really conservative, assume you'll earn $0 until and treat anything earned as a bonus.
Other notes:
Your medical expenses are the big standout to me. Don't risk your health, but do what you can to reduce them. Get generic meds if you can, usually have a lower cost. You have a mental illness, try to keep your life and surroundings conducive to a healthy you, both physically and mentally. If you're healthy physically, maybe it'll positively effect your mental health. If you're healthy emotionally, the same. Really, this isn't so much save money, but optimize your lifestyle as much as possible to encourage health.
Travel - practice travel hacking. Don't fly to DC and Boston, take the train or bus. Also, you can volunteer closer to home! I volunteer every Saturday morning at the animal shelter. But there are thousands of opportunities in your area, look into it.
Clothes - keep looking for the high-quality pieces at thrift stores. I have a good selection of pants available at the closest Goodwill, and shirts are good at a farther one. If the regular location isn't good, try a different neighborhood.