I use a hop spider for my hops, which helps to cut way down on trub. I also use a plate chiller (recirculating first, then right through to fermenter), but don't get a ton of material left in the kettle. I also have/use a Blichmann 10 gallon kettle, where the dip tube leaves a bit behind.
You could make the $10 strainer ball (from a stainless tea ball) like is posted on the boards (is pretty recent). That should help you to leave a good amount behind.
To clean my SS kettle, I use PBW and BKF to clean it. Does an excellent job of cleaning it out that way.
If you harvest the yeast, you can separate the trub from the yeast pretty easily. Just might take another transfer, or two, to get to mostly yeast in the jars. I did harvest yeast a while back, but since I'm working again, I can afford to use fresh yeast.
I wouldn't worry about hot/cold break material if it was me. I almost never see any trace of that left in the fermenter in my batches (and not much is left in the kettle). I would just find a way to keep the hop matter out of the fermenter for batches you plan to harvest the yeast from. Although since I use the spider, I'm keeping a large percentage of the hop matter out of the fermenter in my batches.