All the flowers I mentioned are annuals, except dahlias may be perennial in NYC. Some of my favorite perennials are phlox, Culver's Root, daylilies, iris, and OT lilies...actually I like all lilies!
I don't think it makes any difference when the spring bulbs are planted, but perhaps middle of Oct. would be my choice.
I would plant low growing little leaved rhododendrons against the ivy.....they come in shades of pink....& hydrangea is always nice!