After delegating to a Pool, when should I expect to start seeing rewards?

You will start seeing rewards after two epoch cycles. For example, if you delegate during epoch 468, you will not start seeing rewards till epoch 471. Epochs take place every 5-days.  

Our friends over at Woodland Pools built a great tool that will estimate your payout date based on your stake date, along with a video explaining how the Cardano Delegation Cycle works.

https://www.woodlandpools.net/#/tools/payout-date-estimator