You should. We live in Ottawa near the passport office. I have 4 of 5 passports withing 5 days. No rush was put on it. The 5th passport for my 20 year old male went through a little more investigation and it was at our house within two weeks. 20 Year old was first time as an adult passport, he had a child passport before. You don't mention if its a straight renewal or first time application that may make a bit of a difference but you should still be within you deadline.
Yes, but I wouldn't bother. As long as you get your application in soon you should get your passport in about a month. 20 business days for processing then a week in the mail. However, if you're worried then the money is a small amount to pay to get it nice and early.
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