Reading your description, it sounds to me like your optimism is already fairly balanced.
A lot of trans people have significant baggage to deal with in addition to our gender-related issues. So I can see where your therapist is coming from...it's probably her default setting. But the fact that you're 30, stable, and asking the right questions leads me to believe that you're going to be fine. And with a supportive wife, you're already way ahead of the game.
Women come in all shapes and sizes. Very few have an hourglass figure, and so they learn how to dress for their body type. I'm sure your wife can help you with that. For example, I would never wear a tight mini skirt. Women my age (I'm 36) just don't, and it would accentuate my lack of hips. An a-line skirt on the other hand, gives the illusion of wider hips. And paired with a cardigan or loose top, I can hide my waistline.
My body type is the carrot, or sometimes called boyish figure. And there's plenty of fashion advice online for my body type. And it sounds like you're pretty similar...just 6 inches taller.