Obviously, there are some decisions that only you can make. Whether it's best to buy a smaller contract now and try to add later on OR to buy a larger contract now and work hard to pay for it seems to be the question. You will do better financially through resale. A thought or two I haven't really seen put forth in this thread. You said you wanted ON PROPERTY if I read your post correctly. BW should be doable at $62-65 per point for 150-270 points. LIkely at 150 you're looking at the higher per points cost and at a larger contract, maybe the lower end. The current points availability of that contract should affect the price and value. The closing costs and whether you have to reimburse the seller for points will also affect the final value. OKW should be slightly lower, more available and with more people willing to deal. Also remember that the maint fees are significantly less at OKW than BW, to the tune of almost $200 per year.
If you want BW, buy there but OKW will have lower fees, slightly lower buy in price and you'll need less points to stay there. For the $10K, the best you'll do without financing is about 150 points. Stay away from the buy back programs unless it's at least $10 pp. Don't be tempted to buy off property if that's not where you're going to stay even if it is cheaper. Look at each points package on it's on merrit. Don't discounts packages with no current points, they can sometimes be the best deal going. Also, don't ignore packages with a lot of extra points, they may indeed be worth more to you on a pp basis. You also may be able to buy a smaller package if it has a lot of extra points with it.
You should know that reimbursing the full fees may mean you're paying twice for maint fees on those points. Unlike traditional timeshares, it's not a question of paying this years fees to get this year points. You actually pay for the calendar year, not use year. Any amount you pay at closing is extra money in the seller pocket, not going to
DVC. What's fair depends on the use year, points availability and time of year you're closing.
As for getting it at $60 per point, that's possible but not likely unless there aren't current points. You must decide how much of a gambler you want to be. Remember that it's very possible, even likely, that the price pp will go up again in the next 6 months or so. Resale will go up along with DVC somewhat. You need to decide whether the savings of buying a larger contract of lower pp costs and only one closing costs are worth the financing issue. Also, talke another look at the points tables to decide how many points you truly expect to need. I would build in a cushion of maybe 10% in the total points but it partly depends on what unit size, number of days and time of year you are looking at.
One other strategy would be to buy 150 points or so now and then to add on through DVC when the time comes, possibly in smaller increments. That gives you home resort priority at more than one resort, avoids the need to pay multiple closing costs and allows you to buy now what you can directly invest. Remember also that BW has standard view rooms which cost less points. If you can plan 11 months out and compromise slightly in this area, you can get by with less points. Good luck.