Well, I'm about a third of the way through my playthrough, and it's definitely interesting so far. As I said in my OP, this is only the second time I've ever played Awakening (the first being several years ago, and it being a buggy experience). So far, I think I'm bug free.
I was able to get Velanna's personal quest to trigger by following a slightly modified version of Hydwn's advice above. I started all the side quests at Vigil's Keep, but the only main one I started was "The Righteous Path," along with "Trade Must Flow." The first place I went was actually the Turnoble Estate, and I traveled back and forth from there to the Keep until I got the random encounter with the merchant Lillith to occur, as I read that if you don't get her before you meet Armaas, "Trade Must Flow" will bug and won't complete. Then I went to Amaranthine and only talked to Mervis (I even avoided Delilah as Nathaniel was in the party, and I didn't want anything to screw up.).
After that, I went directly to the Wending Wood where I didn't touch/loot anything (SO HARD!) and quickly recruited Crazy B**** (aka Velanna). We then went to the Silverite Mines (I stripped everyone before we entered.). I did everything there and saved before heading out the door. Right before leaving, I gave Velanna the Shiny Malachite. Travelling back to the Wending Wood didn't trigger her quest for me, so I reloaded and went to Amaranthine instead, talked to Mervis, then headed back to Vigil's Keep. Her personal quest triggered on the way to the Keep. Whew! Now I have to go back to the Wending Wood and do all of the quests, pick up loot, etc. Such a difficult method for my OCD.
One of the funniest things so far was the Dark Wolf reference. When Varel mentioned it, I chose the "lie" option, saying I knew nothing about that. Varel started explaining, and I could imagine my Warden acting all horrified on the outside because of the Dark Wolf's dastardly deeds, while laughing maniacally on the inside because of her sheer Dark Wolf awesomeness. Actually telling the "Dark Wolf" in Amaranthine that I was the real Dark Wolf was fun too. He was quite flustered.
I've decided I really don't like Velanna. I've tried to be nice to her and have tried to peel back the layers of nastiness, hoping that perhaps she was actually a nice person underneath it all. Nope. She is just unpleasant. I intend on recruiting Sigrun next and then leaving Velanna at the Keep forever.
I really hate having to babysit Oghren's approval. What a pain in the butt. Why couldn't Bioware have left him at whatever friendship level he was at when you ended DAO? Felsi finally showed up last night, so I guess I'm doing something right, but it's a big pain.
Nathaniel is kind of adorable. Sure, he's got a big chip on his shoulder, but considering who his father was, who can blame him? We're warming up to each other right now, so things are going good. I think he has a crush on Velanna. I feel I should warn him away from her. The boy doesn't need any more crazy.
I actually really like this version of Anders. He's cute, funny, charming, and just a fun guy to have around (I love Ser Pounce-a-Lot). I don't want to recruit Justice. I don't want him to ruin Anders and turn him into a whiny, loony terrorist (I know this is unavoidable, but I still don't want to do it). And what happened to Anders' physical appearance in DA2? He's pretty cute in DAA. I guess Justice really took a toll on everything. Stupid spirit.