Couple other suggestions, too. Pay attention to issues reported here on TUG. The monthly calendar has not worked well forever. If you see an available date (one day that looks like you can't book it) on the monthly calendar, try that day for 2 days in a dashboard search. Pay attention to your dashboard filters (as you may have to reset them every search).
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As I said, I am diligent. I also keep up with the ongoing idiosyncrasies of the system. Even when I'm not booking something, I'll play around and see how things are working at the moment.
When I started helping my Dad with his account, my sister had wanted to go to Bentley Brook for years, during a really hard time to book. My step-mother would look once and say, nope, not available - or they booked super early and paid full points. Once I started booking reservations, my sisters family went every year til the kids graduated from high school and always on a discounted reservation. Did I mention I am diligent and know the system?
Part of the decision is how much time you want to invest (or waste, lol, depending on how you look at it) looking for reservations. And things change. You have to keep up with how things are working. And if I am looking for a particular resort, I start watching availability, and when rooms might be released (it differs by resort). Like, I can't tell you right now what time of day rooms tend to be released at Clearwater, but if I were trying to book Clearwater, I would know that.
A bonus to being an owner is being able to string reservations together. Not that you can't as a guest, but each one needs a GC. (Not to mention I think Clearwater is owner priority all year now - not 100% on that - you'd have to check). You can book a couple nights, then maybe add on later. Or maybe book a 2nd reservation and have them combine the reservation when you check-in. That could mean you risk moving, that is also very resort dependent (how well they manage the rooms and combine things so you don't have to move). Some you can pretty much count on not moving, some you can pretty much count on you will have to move. But always a risk. Some people don't mind moving, some hate it.
Lots of moving parts. Lots to consider. In the end depends on what works best for you and your situation.