I was wondering if it is worth it to cash in a lot more points to insure getting the type of room you want rather than using less points, making it a gamble? I am Platinum Lifetime and have been in the program for 33 years. I travel (fly) most every week and always stay at Marriott properties. In my business travel I frequently get upgrades. I must admit I don't really put out a lot of effort in this department. For years I used points to take many vacations all over the world with my family. I would always just book a standard room and get upgraded. The past few years we have mostly taken cruises. I am considering using points again to stay at an undetermined exotic location with my wife. I notice now that the point amounts are exorbitant if you want ocean front, etc. and notice that they list point upgrades with cash (definitely not doing that) or upgrades with points. I am just seeking advice since there seem to be a lot of comments about playing the game, so to speak.