If I were you I wouldn't hesitate for even a second in buying points on the resale market assuming you have the cash to do so. My wife and I bought points 5 years ago as we were entering our 60’s and it has been great for us. Both of us have adequate annuity plans and, frankly, have all the cash we need. One problem we have is how to invest the funds that we have outside of our annuity plans. We like Disney and have gone there often since 1973. We decided to pull some money our of an IRA and “invest” it in Disney points. If it all goes “poof”, I could care less. After all, isn’t that what stock market investments do? For us, the bottom line is that the points cost us annually $5 per point in maintenance costs. Do you think we like staying in a studio at the Boardwalk for $55 a night? You bet we do. I haven’t checked recently what my points are “worth”, i.e. what they are selling for, but I’ll bet they’re no worse than my stock market investments.