Have several colleagues who did this pre-Covid. All said the actual flying was fine. It was the rest of the journey that was grinding. To that end, they all focused a lot on consistency — e.g., SeaTac airport parking program, CLEAR, same flights, same seats (close to the front), same hotel, etc. Obviously there will be bad days (after all, you can have a bad day with a regular commute too), but you want to ensure the good days are as streamlined as possible.