Bid The Surface. Not The Water.

Trace the full deck first, then trace the pool the same way — it draws as its own shape in a different color. The moment you close the second shape its area comes off the first, and the Net Area is the surface you are cleaning, coating or sealing. Drag a corner on either shape afterwards and the net follows.

Trace them like anything else — tap points around the waterline and add a few extra through the curves, or switch to draw mode and follow the edge in one stroke. The subtraction works on any shape you can outline, not just rectangles.

Pool Deck mode is built for one pool in one deck. For anything else with holes in it, like a parking lot with islands or a patio with a fire pit, use that surface's own mode: trace the lot, then draw each island or planter with the Cutout button and it comes off the total, as many as the job has.

Use one of the other modes instead: driveway, patio, sidewalk, deck, parking lot or snow removal, each one total, traced as one outline or as several sections that add up. Switching out of Pool Deck keeps the address but starts the trace again, because the job no longer needs a second shape.