I hunt out of a boat to. I can set up in about 20min. if I am putting out a BIG spread. When I pick up, I use the electric motor, and have my buddy hooking dekes. I put them in the boat, not the bag. After I have the boat on the trailer, we wind up the anchors and put them in the bags. This way I can get off the water faster, and be in before it gets to dark. I have lights on the boat for running out, and setting up, but I don't like coming in when it's real dark.
I don't have any problems with tangled lines. I have made a "slot board" out of 1" grey conduit that I have on each side of the boat with a slot in it for the line to go. The weight rest's in the coduit, and rides fine to the trailer. It's easy putting them in the bag after I get in.
Take care of the dekes after each hunt, and you will have a pleasent hunt setting up!! Save yourself some time by not dealing with tangles.