First rule of renting - thou shall not finance a
DVC purchase to rent. In other words, buy only the most amount of points that you can pay cash for because the timeshare interest rates are outrageously high. The magic number seems to be to stay less than 20 reservations per contract in one year, but I have never heard of any DVC member that actually had a problem as a result of renting their points. To answer your questions directly (and the answers can always change depending on if and when Disney changes the rules) - You can always buy more points than you need and rent them in a variety of methods and venues, but I would urge caution with this plan as there are risks and hassles than may ruin your fun and cash flow. I can only tell you that some people enjoy renting points and some people hate it as it really depends on your own individual personality. I would discourage you from thinking DVC point rental is some magic investment that will beat stocks, bonds, CDs, real estate, annuity, etc. You are WAY better to NOT think of DVC as a cash cow and simple a pre-paid discounted vacation. If you are really set on buying more points to rent, then one of the better strategies seems to be buy 2x the points you want (or really need) and then rent 1/2 the points you own and then use that money to pay your annual dues. This will (technically) allow you to buy DVC and never pay out of pocket money for annual dues (in theory). The monkey wrench is that most renters forget to account for the original investment costs and lost opportunity costs of that investment. When you do that, most people find renting points is not that great an investment. On the other hand, if you can buy a really cheap resale unit, then it can pay for itself in about 8-10 years and the net cost after than is $0.