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Basically, to even download the 400 Days DLC on Steam (even after buying it), you'll have to first download Steam's version of Season 1. I don't think you'll be able to transfer the DLC data to your retail version, but you'll already have the Steam version installed and they should use the same save files (including prefs.prop, an important file), which are hopefully in the same location (if not, move them there - see below), so you should be able to continue in the Steam version where you left off in the retail version - all your decisions saved and ready to start 400 Days.
Back up your save folder, including prefs prefs.prop before trying any of this. For me that would be "...\My Documents\Telltale Games\The Walking Dead\", where there're a bunch of .save files, a prefs.prop file, etc. Also check to see if there're any prefs.prop files in your game folder under "...\Pack\" in any of the subfolders "default", "WalkingDead102", etc and back them up, too, if they're there.
Hope I was able to make things clearer and not more confusing. :)
You can buy DLC without owning the base game. I just checked with Black Ops 2 and you get a warning stating it requires the base game. As 400 Days is fairly cheap you could just buy it and test it. Worst case scenario you have something you could trade with someone.
Thanks for all your replies on this matter. I looked on amazon.co.uk friday and found Walking Dead season 1 GAME OF THE YEAR EDITION including the DLC 400 Days. Then I discovered although it was on Amazon they didnt actually have it. It said on the page get it from these sellers. I am always a little picky who I purchase games from. I know it should be safe with Amazon but you can never tell. Am I the only picky one out there.
I did check on the Walking Dead Season 1 menu screen. There is a DOWNLOAD CONTENT section. Alas it only shows the 5 installed episodes for Season 1 I have.
I get the same warning message for DLC 400 Days as well. Which means I would still need the base game on Steam to be able to play 400 days. As I have the retail version of Walking Dead Season 1 it would be pointless of me to just download the DLC, when it wouldnt be compatible with my Season 1 shop-bought game. It looks like I am out of luck.
Hmm, maybe try looking at Telltale's support forum at http://www.telltalegames.com/support/categories/support-walkingdead-pcmac.
Sorry you're having so much trouble with this. All I can say, otherwise, is wait for a 75+% off sale (happens often enough on one site or another - here, Amazon, GMG, etc) and buy both the base game and DLC and continue the game with your original saves, but playing the Steam version instead, like I said above.
I have to say, I didn't think much of 400 Days - the stories were too short to really get me interested/invested in the characters the way I was with Lee,Clementine, etc., but I understand being curious about it anyay :)