You can get the color pictobox on your first playthrough by clearing a sidequest on Windfall and finding a firefly at the Forest Haven. Any figures you get the first playthrough transfer over to the second.
Check a FAQ to see the missable figures, because there are a LOT.
The terms "casual" and "hardcore" are meaningless, please stop using them. Deconfirmed is not a word.
The thing that deterred me from completing this quest originally was the fact that you could only hold 3 color photos at once - it made getting boss shots a lot more difficult, and the trips to and from Forest Haven and the constant Wind Waker animations made it really tedious after a while.
Glad to see they fixed all this.
"It's dangerous to go alone! Take this." 3DS FC: 3909-7604-9701
See, my first thought was "%$#@ I'm going to have to do all that again." I'm kind of neurotic about completely beating my games...
At least it'll be faster this time due to the changes.
And in regards to the OP, you can get the Deluxe Picto Box as soon as you reach Forest Haven, by catching a firefly and doubling back to Windfall. Which means that it's completely possible to do it all on the first playthrough, even though all of the figurines carry over into the 2nd playthrough. You won't even have missed anything, since Gohma can be photographed during the rematch in Ganon's Tower.
You can get the Deluxe Pictobox even earlier in the HD version. You don't need the Firefly anymore, you will get one as soon as you become Genzo's apprentice. Which means you can get it on your first visit on Windfall, even before Dragon Roost.
I've also heard that the camera now tells you when the shot of a person or monster is "great", which means it will get accepted by Carlov. This should make collecting the missable figurines (like Helmaroc King, Tetra, the Wizzrobe Master, Cyclos or Puppet Ganon) much easier, because you know in advance that a shot is good enough, which allows you to save before heading to Forest Haven.
It was possible to get all figurines in the 1st playthrough of the original version, but not easy. Now in TWWHD there's no excuse not to complete your entire figurine collection on the first playthrough. It makes me even wonder what the 2nd Quest mode will be there for except for having a different outfit and being able to read Hylian...