Streetcar
Veteran Member
Second the idea of separate structure that is tied to original. Not many buildings are designed to carry that much additional load.
Attach it only for looks. Put in posts next to the house to actually carry the load, and make only a very light attachment (even slightly flexible) to the house for the HOA purpose. I would use engineered web joists to make the span.
If the walls are 8" think it sounds like you have room to open them up and sneak in a steel column here and there. If you think it would fly, you could even run them up the outside of the existing wall, and encase them as part of "trim" or "brace walls" for your "addition"...? You say the new structure has to be tied to the existing. You don't say it has to carry it.
On the plus side after the next big earthquake levels the house we can live under the deck.