I have been flying electric for a long time, generally, in the fall, my cutoff outside temperature is about 45 degrees. Cooler than that and my fingers start to get numb which hinders flying. This is for R/C. For C/L, since you are pretty much walking all of the time, my cutoff is about 40 degrees if sunny and not windy.
When getting ready to fly in cooler weather I will bring the batteries up from the basement and let them warm up in the main living area of the house (still stored in a steel box). Overnight that brings them up to room temperature, probably around 65 degrees. While at the field, I will lay the batteries on top of the dash hopefully exposed to the sun with the car closed up. On a sunny day, the interior of the car will be nice and comfortable and that is how I keep the batteries warm. When getting ready for a flight I simply walk up to the car, grab a pack and go fly. I have been doing this years and it works well enough. I fly R/C pattern as well (2x5S packs, 4000-4500 mah) and it works well for the larger packs as well. If I do any field charging, I use my pattern packs which have been retired; they can still deliver enough power to charge the smaller C/L packs. My charger allows for a 24v input, so I normally connect two 5S packs in parallel to power it. Out of this, I can normally get a 6S, 2200 mah pack four times.
I try to balance battery use I to try to use the newer packs more frequently than the older ones; that means that the new packs get flown first and potentially get re-charged at the field for the last flights. A good day of flying is generally about 8 flights; after that I really start to get sloppy.