1. Depends on the trip. Swimsuit, gym shorts and a t shirt, running shoes that can be used for the gym and going out, a pair of jeans or shorts with a nice shirt to go out on the town in. I bring my laptop out of personal preference. Some guys just use the company iPad for Netflix and web browsing at the hotel but I like my laptop. Get a second dedicated set of toiletries that stay in your bag when you're home so you don't have to mess with it. Name of the game is packing as little as possible but still having what you need.

2. Tough but doable. You'll need a cooler to bring with you loaded up with food. Buying a Food Saver and wrapping up meals can save space. Save space in the cooler by putting only your food that needs to stay cold in it and put the non perishables in your overnight bag. You can buy ice packs and hope that your hotel fridge has a small freezer in it to refreeze overnight. Otherwise you can get some freezer bags and fill them up with ice before you leave the hotel at the beginning of the day. Lots of crew cooler bag options. A nice cooler/EFB setup is the Aerocoast Pro EFB + Cooler II Bag. It's not easy bringing food but having healthy options with you is important. And you'll save a lot of money as well.