I can't offer you a perfect solution, but after seeing the ridiculous piping job that was done on my place when I bought it, I decided that a complete redo was in order.
I have a typical jet pump on shore that pumps up to the camp and draws out of the lake. Everything was put together with threaded fittings, the pump was out in the weather and the electric (110) was done via a junction box that was just thrown on the ground and mind you with no cover on it. Unacceptable!
First thing I did was to install a weather proof and covered gang box on the side of my deck at the water. I installed a GFI outlet and isolated the circuit back at the main panel in the house. I then poured a small concrete slab to put the pump on and built a "dog house" to cover the pump and protect it from the weather. I wired in a new cord from the pressure switch that will just plug in to that outlet I installed. If it's a 220 you can use an L6-30 twist lock. With that all squared away I pulled off all the plumbing fittings and replaced them with quick release cam locks. These are the bomb!
http://www.camlock-fittings.com/ To prime the pump I also installed a vertical filler with a cam lock as well. These cam locks can be bought either online or locally. I got mine at the well/pump shop in Alton near the traffic circle on 28.
For deploying my draw line I use a simple milk crate and run the end of the hose through the handles of the crate and tie it off so the end of the line can't be pulled out. I then attach a rope to the crate so I can lower it into the water gently till it hits bottom with a couple of rocks to weight it down. At the end of the rope I tied a loop that is easy to grab with a hook for removal in the fall. One thing that could be done different is to tie a rope long enough to the crate to reach back to shore and tie to a tree leaving it submerged on the lake bottom.
I never get wet when I deal with my system and with the cam locks installation and removal is a snap. The other nice thing with those cam locks you can get a plug to seal the ends of your lines over the winter time.