The secondary in this case is just to get the dry-hopping flavors in the beer. I would put it in the bottles, and then wait for it to be ready. Dry-hopping generally only lasts for a week or so, so I wouldn't do another week.
A DIPA may take a while in the bottle before it is ready. I'm not recommending another week in secondary; I am recommending more time than you probably think is reasonable in the bottle before drinking. Try one a week to see how it develops if you must, but don't do any more or serve it to anyone before at least 4 weeks have passed in the bottle. This will be hard, but it is necessary if you don't want others to get a very bad impression of your brewing. Or a lot of kind, insincere comments. Beer takes time to be good.
Oh, and keep test bottles in the fridge at least 2 days before sampling. You'll get a gusher, followed by a flat beer, otherwise. At least if it's carbonating properly. I've had a lot of people comment about my 'carbonation problems' before I realized this. CO2 takes time in the cold to dissolve in beer.