Not necessarily (barring a long stay in a Fairmont or Sofitel) because you can get Southeast Asia 5-star beach resorts at below US$200/night, and discounted food does not add as much as you might think. I recently spent several nights at a M Gallery property I really liked (no beach) and it was below US$100/night for a beautiful new 5-star room.

Also wondering how to capitalize on free 20 Status Nights.

Incidentally is there any bonus for focusing on one particular hotel brand? For example, if by coincidence your next 5 planned trips are all with Pullman properties, no harm in telling the 5 managers about it in case they give you something?