I've only tried double flared once, and I couldn't really get the hang of it. :/
The problem with double flared is that it's the smaller center section that's your gauge, and the outside is larger which is what causes most people trouble.
I personally wouldn't recommend them for a fresh stretch because of that, you don't want to accidentally damage your lobe.
I read somewhere that the best way to insert them is "like a button". Tilt it and put in one side first, then the rest. I've not tried it myself though.
PS. "gauge" isn't the name of the jewellery, it's a term of measurement. They're tunnels, not gauges.