What size line for the painter and how long? 40 feet?

I am making a shopping list.... this idea just sounds great.

4.4 # Bruce
8 feet of 1/4 chain
20 feet of 3/16 shock cord
Polypro line from HD... 3/8 hollow braid

and a painter... what size and length. Right now I am using an old stays'l sheet... so it really isn't that long and probably heavier than I need.

Oh yeah, small orange bucket to stow it all in. GRIN

Also I want a better tow line... right now I haul the dink right up to the stern and just let the stern of the dink ride in the water... it is an airfloor, so pretty light. I saw a nice towing bridle the other day that just made sense... but the freaking things are way overpriced. It was a strap that went to a float that went to a floating line. I think I can rig that easy with off the shelf stuff far cheaper than what I saw... just looking for input on what size line to use.