I am stingy till they bleed. A lot of people look at every nuance when they are looking to buy and hardly think the "cost" after they buy. Their choice but seems dumb to me. I think a lot of people treat
DVC like found money much like you got an inheritance, that when they spend it, it's not really like spending real money. Their choice of course but not a good one overall. The exception would be use or lose points.
Are you doing two weekends for those 9 nights? I would generally prefer to do BWV prior to SSR because I generally follow and believe in the travel recommendations of doing the busier part of a split trip first. If you can get BW view or SV, that may save you a few points but likely not enough to sweat over.
Having said all of that you need to learn the system well enough that you won't have to second guess yourself very much. Then you'll be comfortable with your decisions as well as any changes you need to make.