I'm in the same boat often, paying 20,000 for a RI that I could probably get for $99 at times. Problem is that I have too many points, too little time and they sit there devaluating. So I treat other families to rooms when traveling on weekends for kids sports, often they drive me and treat me a bit so its a little nicer.

My answer is NO if you are confident of using the points in the near future for something better, nicer, bigger, longer, etc and YES if you feel they are going to sit there unused & waiting for a period of time.

And about one cent per point seems to be the bare minimum earn / burn ratio most folks try to use. But you have to do what makes sense for you at your particular stage in life... Waiting for retirement like I previously thought is a lose-lose situation with annual / bi-annual "enhancement" devaluations.