awful blurb about ra'eena
Her main guild is the Thieves Guild, though it is her second that she was initiated in. (First was the Dark Brotherhood, though she's the Listener, she's separated herself from them quite a bit. Shadowmere is the only reason she doesn't feel too bad about the whole sorta-indiscriminate killing thing.)
She's always quiet and stealthy, even in areas (esp dungeons) where there are much lower level enemies. If there's an advantage to be gained, why not take it? She's also likely to let her companion attract their attention, then flank them.Her pup, Sceoland is a huge help in keeping the attention off of her.
She's most definitely not evil, nor a true bad person. She tends to not be malicious, unless someone is being bigoted (moreso than the usual Nord bs) or a bully. She favors those that are poor, and weak. She has no issue sparing a gold or two for beggars, especially if they aren't belligerent about it.
Let's see. She uses Borgakh as a Soul Gem farm. Doesn't love enchanting, but she's decent at it, and her company must always be kitted in relevant enchantments. She can slap potions together, but she's never sure what exactly is going to come out of the ingredients. She doesn't forge, nor improve her weapons, she leaves that to others.
It's difficult to sell things. She may need it later. Or someone might need it later. Growing up with nothing, and no one, has made her very materialistic.
Now, however, she lives in semi-luxury in the newly constructed Lakeview Manor, with her wife Ysolda, a chicken or two, a colossal garden, and no children (eva!). Ysolda has been with her since the very beginning, before she had her own place in Whiterun.