I would start with new windows, and then do the paint. You don't want the window installers and painters tromping on your new landscaping. Meanwhile, you can develop a plan for the new landscaping, including any hardscaping changes you need to make for the deck, patio, and hot tub.

By the way, rock mulches are not good for plants, unless maybe they're cactus. If you don't want regular mulch, install low growing ground cover plants to cover the ground between your new trees and shrubs.

Windows.

Deck.

Paint.

Hot tub.

Landscaping.