I really can't say that I have any regrets because I bought what I could afford at the time. I didn't want to finance so I stuck to my budget at bought my first contract at SSR and my second one at HHI with cash. My SSR contract of 160 points gave us a good base of points to use anywhere while my recent 150 points at HHI was purchased to stay specifically at HHI. Getting in HHI in the summer at the 7 month window can be near impossible so having that 11 month window is key.
The only thing I understand differently now is the lower cost of paying cash for some trips or some nights. I have found that the cash option if often a better deal than using points considering the cost of purchasing the points, the maintenance fees, and even the rental value of points. If I were to do it again I would almost want a minimal amount of points to get my foot in the door and then invest the money I spend on DVC and use that invested money to pay cash when we wanted a DVC vacation. But oh well... its only money.
The only thing I understand differently now is the lower cost of paying cash for some trips or some nights. I have found that the cash option if often a better deal than using points considering the cost of purchasing the points, the maintenance fees, and even the rental value of points. If I were to do it again I would almost want a minimal amount of points to get my foot in the door and then invest the money I spend on DVC and use that invested money to pay cash when we wanted a DVC vacation. But oh well... its only money.
with HHI. It is such a great vacation. So I guess I lucked out. I am a teacher and would never head to WDW during spring break or summer so HHI is great for us. ( When I fist bought I was not working.. this wonderful economy has led me back to work). So I am VERY happy with my contract. I did add on with Disney 50 points at BWV which I really enjoy as well. I am usually behind on points (borrowing) but I have never had a trip I could not take so I guess that it OK. 
We got spoiled by a 1 B and now have..for the first time.. borrowed points to be able to stay in one for Easter Week. One day we will add on, but for now we borrow.

