Lots of good questions.
So for WKOVRN 2BR OF, we will get 8325 DPs EOY in its use year. I have another EOY that I get points for so to me, it works out just fine whether they are annual or EOY. For status, MVC averages the points as if they were annual. So that means 8325 are divided in half to figure out your status level but awarded in the usage year. Since you can bank and borrow points, the year awarded makes less difference. It does help that I am Presidential so I get 1.5 years to use the points after I bank them. There is no fee to bank points. I have never borrowed so I am not sure about that. I have not heard of a fee for borrowing.
In terms of how many vacations you can get from 8325 DPs, it is really quite a lot depending on the unit size, season, view and location. A few examples of things I have booked using DPs:
4250 DPs: Marco Island 2 BR Gulf front in June (there are many view categories here but this is the highest view category, which I booked for next summer)
5725 DPs: Ko Olina 2 BR Ocean view (equivalent to ocean front at WKOVRN) in summer (can go as low as 4925 DPs in shoulder season)
3675 DPs: Ritz Carlton St Thomas 2BR suite (all oceanfront at this resort) in summer - on our way here now, assuming we ever get here. Our plane has mechanical difficulties!
5875 DPs: Waiohai Beach Club in Kauai 2 BR Ocean View in summer (can go as low as 5025 in shoulder seasons…however most people think island view at this resort is just fine…I think it’s because ocean views at this resort are not as incredible like at other resorts so island view saves about 1000 DPs or so)
For Marbella in Spain, the 2BRs are mostly high 2000s to low 3000s in DPs with a few high weeks in the summer being a little over 4000 DPs. Just giving some more examples to show how many vacations you can take using 8325 DPs.
For the above, you use a lot fewer DPs if you chose a different view or unit size and more points if you choose a higher season. But very few locations are going to be over 6000-7000 DPs even in high season. Maui is probably the highest in the program.
You can take a look at the points charts here:
Nowadays, I book when the booking window opens to get exactly what I want. Prior to Covid, I was not having to worry quite as much about the booking window.
To me, the most attractive part of qualifying my Vistana week is I can get more vacations at more destinations in what I consider to be equivalent view types in 2BR units for 8325 DPs. If I lock off my 2BR at WKOVRN, then I only get a 1BR and a studio. If I want to visit other VSE resorts, I need to use SOs at 8 months when most inventory I would desire would be unavailable. I also prefer booking at 13 or 12 months, depending on when the resort opens its inventory for booking with DPs.