A lot of different things can happen with DD.
With no drogue, you can get the upper section going nosecone down, pulling the fin can with it and actually falling ballistic. Long shock cords can be fatal in that situation because the main opens and then the upper falls to the end of it's cord, and the fin can fall past both and hits the end of its cord with a lot of force.
With no drogue, you can get the fin can falling almost flat, just slightly fin down, and it will actually fly that way, pulling the upper section with it. If you're lucky it will be flying into the wind, if your unlucky, it flies with the wind. Either way it can add a lot of horizontal distance to where the rocket lands.
With a drogue, you want the upper section to stay at or above the fin can. I prefer to have the upper section well above the fin can so the can stays pointing down and you don't get any of the flying effect.
The size of the drogue you need can be a trail and error type of thing. I tend to start larger and work down until I get it falling the way I want.
I also make my own drogue chutes that are about 3/4 as tall as the diameter (almost cone shaped), and have relatively large spill holes. This seems to work quite well as the drogue stays stable while falling fast. Drogues without spill holes seem to spin and shake side to side very quickly when falling fast.
As for needing heavy duty chutes, not really. Most of my main chutes are made from old umbrellas. They are not rip-stop and were made in China. All I've done is sew the shroud lines on. I have a golf umbrella, 53", I use as a main for a 10 lb rocket and it's never had an issue. I also always use a drogue and keep the upper section above the fin can so the cord is stretched out well by the time the main opens. It never has a large shock load on it.