Plane travel is very simple, if you follow all of the regulations. You can take all of your makeup with you during the flight(s) as long as it follows the rules. In my opinion, it's always easier to apply long lasting or waterproof products before taking off because it will be another item to keep track of, but it's your call. All of your liquids are to be in bottles under three ounces. Some airlines have some wiggle room by tenths of an ounce, but I wouldn't count on it. Zip those liquids into a quart size bag. Everything else can go into your makeup bag. Why don't you take a look at the 3-1-1 rule at the tsa's website.I find that it may apply to you, but it's just going to be too much to write down here. So go check it out :)
*Try to pack as light as possible because you don't want to have a lot of potential products to lose on the plane.
*Look for your favorite products, just in mini sizes. Much handier!
Good luck and I hope you have a fantastic vacation!