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I usually just carry everything so I try to pack as light as I can. Do you have to fill the 5 gallon insert
I have used an igloo water jug many of times . Works good to keep them from freezing on the ice but when I get home I bring in in on the back porch . Also you don't have to worry about it falling over and spilling all the water out .
Walking to and from the ice you don't need to have it "filled", but need enough to keep bait alive. Once you start drilling holes you can add more water from the lake. A sled of sorts would help conciderably to take out your gear. "Smitty sled" is compact, portable, cheap, and easy to customize. http://www.iceshanty.com/ice_fishing/index.php?topic=103927.0
put 'em in your mouth!
Let me guess you learned that from one of your old fishing buddy's .
Nah, drunken college dare but I had to swallow them.
...but speaking of old fishing buddy's, If I told some stories about the Hillbilly that took me to Erie every weekend trolling, You guys would be thoroughly entertained!
I also use the 5 Gal bucket with the white foam insert, with an aerator and keeping the lid on it you should not have any issues. We use them in Northern Mi and have not had them freeze even left out all night in the single digits unless the aerator quits.