The point about crusing is that everyone finds what works for them and makes the most of it each time they have a chance to sail. That said, I'll weigh in on the anytime vs. assigned seating debate. There are absolutely pros and cons to each option. We did not like our first assigned seating cruise. It just did not work for us. We LOVE anytime dining. This is what we would suggest to make the most of anytime dining. 1) ALWAYS make a reservation. Check out the Princess Patter and decide what time you want to eat. Call and make a reservation. 2) Stick relatively to the same time for the entire cruise and more importantly ask for your same server, you'll find that you have a very easy time of it. We live in DC and waiting for 15-30 minutes is a reasonable time to wait for a table. If you make a reservation however, you won't have to wait long. 3) Have a drink at the bar while you wait. If there is a wait for a table, they give you a pager, go have a drink and enjoy being with your partner or friends while you wait.
We love being able to have a table for 2. We work too hard all year long and to have a week where we can eat together--no matter how long we have to wait--is well worth it to us.