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If i'm not mistaken (it's been a while since i had a char play through Cadwells quests) the Gold quests do not unlock until you complete the Silver quests.
I have no idea what will happen to those quests if you were to finish the Gold ones first (obviously without having Cadwells Gold active at the time)
You can start doing the quests, sure. However, Cadwell won't give you Gold until you've finished Silver.
Both Cadwell's Silver and Cadwell's Gold are supposed to be able to be completed retroactively (i.e., if you complete the related quests before picking up Silver and Gold, Silver and Gold complete themselves automatically)... however, I have heard that it sometimes doesn't detect completed quests correctly. So be careful with it.
Edited by BlackSparrow on February 13, 2017 9:50PM
Living vicariously through my characters.
My Girls:
"If you were trapped in your house for, say, a year, how would you pass the time?"
Nephikah the Houseless, dunmer assassin: "I suppose I could use the break. I have a lot of business holdings now that need management." Swum-Many-Waters, elderly argonian healer: "I think that I would enjoy writing a memoir." Silh'ki, khajiit warrior-chef: "Would this one be able to go outside, to the nearby river? It's hard to fish without water!" Peregrine Huntress, bosmer hunter: "Who is forcing me to stay inside, and where can I find them?" Lorenyawe, altmer mechanist: "And why would I want to go outside in the first place? Too much to be done in the workshop." Lorelai Magpie, breton master thief: "I'd go nuts. Lucky for me, I have a little experience sneaking out!" Rasheda the Burning Heart, redguard knight: "I would continue my training to keep my skills sharp." Hex-Eye Azabi, khajiit daedric priestess: "I suppose it would be lucky, then, that I built a shrine to Mephala in my backyard." Yngva Stormhammer, nord bandit (reformed...ish): "I hate being inside even when I'm not forced to be. GET. ME. OUT." Madam Argentia, vampire dunmer aristocrat: "I suppose it would be more of the same. I have a rather... contentious relationship with the sun." Mazie gra-Bolga, orc scout: "Uh... I'd have to house train my bear..." Felicia the Wanderer, imperial witch-for-hire: "What Lorelai said." Calico Jaka-dra, retired khajiit pirate: "This one would like a rest from her grand adventures. Her jewel shop runs out of stock!" Shimmerbeam, blind altmer psijic: "Provided that I am confined to Artaeum, I do not think I will want for things to occupy my time." Shauna Blackfire, redguard necromancer: "Sounds like paradise. I hate people." Kirniel the Undying, cursed bosmer warrior: "I would feel useless, not being able to fight." Echoes-from-Dragons, argonian who thinks she's a dragon: "All the better to count my hoard!"
But, there maybe an issue if you finish Gold Content before you finish Silver Content. So, do all the Gold Content up until the last one for Gold in Zone 5 (the last boss battle basically), then go do the Silver Content and complete that, then go do the last quest in Gold. Your Journal can help you determine the last quest for the Gold content for your alliance so you know when to switch to the other alliance.
Note you wont be doing this as Silver and Gold, you will just be doing the content. You can talk to Caldwell twice (leaving the Harborage in between) after finishing the content to get the Silver and Gold rewards.
Edited by Nestor on February 13, 2017 9:49PM
Enjoy the game, life is what you really want to be worried about.
PakKat "Everything was going well, until I died"
Gary Gravestink "I am glad you died, I needed the help"
No, gotta do silver first, then you will unlock gold.
Wrong. SInce One Tamriel.
You can do the quests in whatever order you see fit. THe correct order makes more sense in terms of storytelling, of course, but you can still start wherever you want, or do it completely backwards.
That being said, the actual completion/validation of gold/silver achievement is a different thing. Silver will only start once you've completed the main quest, and Gold will only unlock once you've completed Silver.