We bought 50 points direct because we wanted to finance* and go every three years in a 1BR. We end up with 15 straggling points which I have been able to incorporate into WDW bookings at 7 months. Since we want a 1BR at HHI (there are only 21 of them, and only 21 studios too), we knew we would need the 11 month window. I did look for a 50-75 point resale contract, but after 6 months, I gave up and bought direct. The timing worked out well since we have a Feb UY and made our deposit on January 29. I had our points the next day and we were able to bank them 2 days before they expired. Now that our girls are "older" (11 and almost 14....but have been to WDW almost every year since they were 2 and 4!), we've discovered that we really enjoy HHI a little more than WDW. Now, I am tasked with getting lucky with our AKV points at 7 months, or trying to save up and stalk for another 25-50 points at HHI.
*I know that financing is not a good idea, but let me explain...
...We had a bank account used for our DD's pre-school tuition and we had been putting $25 into it every two weeks for three years. It was a direct deposit from my paycheck so I never even saw it or knew it was "missing". When she started kindergarten, that account was no longer needed. As it turned out, the cost to finance our 50-point HHI contract amounted to $49.08 per month...which was almost exactly the amount we had been depositing into that account for 3 years. I figured since we hadn't even noticed it for that long anyways, we might as well continue to use it as a payment account for the add-on contract. I've made a few extra payments along the way so it will be paid off a little early, but overall, it was a "painless" expense.