I've never used floating dip tubes, haven't had a need for them (yet). It was just an idea to get around sucking up the trub, or prematurely plugging up your dip tube or screen/filter.
You've got a point there, how do you fill the keg without the long diptube being present? Have you looked for other threads on that topic?
Here's the way how to purge the remaining Starsan/water, once your floating dip tube bottoms out:
Leave some pressure in the keg, say 6-10 psi. Disconnect the gas QD, invert the keg, and stick an open gas QD on the gas post, over a bucket or bin to blow out the remainder of Starsan or water. Voila!
Re: cold crashing
The lower the temp the better/faster, but anywhere under 36F should do fine.
I put my ferm buckets in a temp controlled freezer at 32-30F. Depending on the yeast used, some beers are crashed almost completely within 24 hours, most take a few days. Lagers take a week, or 2, before they're acceptable.
If you use a cooler chest, you need to cover it with a thick sleeping bag, moving blankets or so, to keep the cold in, or you'll go through a ton of ice. Or put the whole system inside a rigid foam box?