Not going to look very good, and will be pretty expensive. Explore another plan.

Seek local professional guidance.

Thanks for the comments. I did ask a truss manufacturer who advised me to abandon the shed roof and just build another story above the garage. I like the shed roof style as it gives me a way to easily get up on the roof and does not create more living space to heat, cool, and pay taxes on. I guess I could finish it out and use it as a rental or a guest room. It just isn't what I was looking to do.

A truss manufacturer isn’t an architect. A roof need not be trussed. And a 100K project shouldn’t be planned by those who lack design talent, and engineering experience.

Why don't you just build a pole barn garage? It's cheaper than adding on.