Just a quick breakdown of what I did... the same as above goes for the bag. I had both the strongbag and the eBag... eBag was better constructed, but the strongbag was bigger, so it's a tradeoff. My strongbag zipper (one of the two) broke a few months ago and wouldn't zip and the 'thermal padding' is falling off/apart. The eBag is still going strong, but it still is smaller and well... it's smaller. So, once I start working again - I'll bring the strongbag out of retirement or buy another one.
Instead of ice, and baggies, and headache bags, and etc. my trick was the non-carbonated drinks from the galley - start with frozen food on day one to keep everything cold, as you eat the food replace the empty space with 'soda' cans... (non-carbonated) grab drinks from the galley and freeze them in the little fridges on overnights, or in the winter in MI I would just leave them outside... and on day 4 or 6 before the commute just throw them back in. (also works if you throw drinks under the ice in the galley - if you don't have a fridge the night before - they will keep stuff cool most of the day)
Oh, no fridges on overnights... take the trash can from your room to the ice machine and fill up the sink with ice and your food, throw a towel over it and you have an instant fridge for 14 hours. Anything longer, (like that happens...) throw some more ice in.
Ok, to the meat... GET A FOODSAVER. What I would do is premake 10 of the same thing each time on my days off (or when time permitted) - turkey, ham, meatloaf, mexican lasagna... I have a ton of recipes I've developed - basically homemade frozen meals. Well balanced, low sodium, mostly organic, very healthy. After you cook, portion out, freeze, throw in the bag, vacuum seal them and there you go... 2.5 trips worth of food, as long as you keep up with it and keep them frozen the meals will last a few months in your freezer and you can always grab a variety when you go. As long as you keep up with making a variety. (now, we have a deep freezer, so we don't get freezerburned meals - a standard freezer wouldn't make the stuff last as long, so plan accordingly) Oh, with veggies, grab the pre-frozen bags and transfer frozen veggies that you buy at Trader Joes or whatever directly to the pouch when you make the meal - when you reheat, the veggies turn out perfect.
On Day One before the commute I would grab my entrees, along with frozen portions of lunchmeat and cheese i've portioned into baggies. (There's a great deli-mart in Simi Valley with dirt cheap lunchmeat - or buy in bulk when stuff is on sale, portion it into baggies, freeze, and a couple of months later when it's on sale again buy again... oh, and Turkey sheds it's water when frozen, take that into account) I carried around little bread containers that I bought at Ralphs... (and if you don't know what Ralphs is, watch The Big Lebowski) they were very cheesy, the said Crayola on one, Wonderbread on the other, and I think I had one with characters from the movie Cars. But, they were shaped like bread and I could put a package of sliced sandwich bread in them and they wouldn't get smashed.
I was legendary around ORD at my ex-PHX based regional for being the 'guy that brings his food' - It would save me about 200-300 bucks a month. (Figuring, Breakfast at the Hotel... $7 for Lunch, $13 for dinner - 20 days on the road = $400. The way I did it was about $100 in materials each month, so $300 savings from eating out.)
And, to conclude, here's something that I was thinking of trying before I got furloughed if I didn't want to cook that is DIRT CHEAP and HEALTHY. I'll throw it out there: Use your favorite search engine (the one that starts with G) to search for: angel food ministries. It's a great charity that uses churches to get inexpensive food to people in need. (and you, or anyone...) Click on 'this month's menu' and look for the Senior/Convenience Box. $28 bucks, 10 meals... transfer them into a food saver pouch, shrinkwrap, and done... $2.80 per meal. Grab two of them and you've got 20 healthy meals for the month for each overnight. I'm thinking of picking up some of their regular stuff for my family now that I am on the 'furloughed budget' - I would have tried their pre-packaged meals before this, but I admit, i'm picky. Very picky about my meals and by making my own food I could control he meat to starch to veggie proportions.
I hope this helps... let me know if you have questions or if anyone wants my old foodsaver before I Freecycle it.