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Domestic US Carry On Luggage questions

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It's been a long time since I tried to get away without checking a suitcase. BUT, I will be traveling for a 4 day weekend to Boston and would like to get away with it. So, here are a couple of questions:

1) Carry On Liquids - get a quart size Ziploc bag and I can put 3 3 oz. bottles of makeup, moisturizer or eye make up remover? Are powder blush and powder eye makeup OK? How does eye liner and mascara count?
2) I will have a roller that measures 45 linear inches (Delta says this is OK). Can I bring a large tote bag in addition to my purse? What about my raincoat - can I carry that on? Can I just stick my umbrella in the raincoat pocket or is that counted separately somehow?
3) I would like to put my dress in a store label dress bag (not really luggage) so I can lay it flat on the plane. Can I bring this or does it count toward carry on?
4) If I go shopping in Boston and have stuff in a shopping bag, is that item #3 in addition to my roller bag and tote?

This is very confusing, but I appreciate your help in advance. Thanks!

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