Purely from a financial standpoint, direct purchases can't compete with resale. Take Copper Creek as an example. Direct price is $250 per point. You can buy resale for $150 per point. So on a 150 point contract you would save $15,000 purchasing resale. And remember, if you are financing instead of paying cash that difference is magnified due to the interest on the additional $15,000. I don't see how the discounts (food, merch, annual passes, etc..) could ever close that gap. So if the money is the key factor in the decision, it's better to buy resale and just know that the discounts you are missing out on are far less valuable than the cash you saved on the purchase. Now... I get it... people buy direct for other reasons. I think the three most compelling "non discount" benefits are member events (such as Moonlight Magic), member lounges, and use of ALL properties (right now that means Riviera, but soon it MIGHT mean others, such as the new Poly tower). Most remaining benefits require you use points for things like cruises or the World Collections, and I have never found those to be a good value for your points. So are are lounges, Moonlight Magic, and Riviera access worth $15,000+? For us the answer was "no". For others the answer is "yes". Different strokes for different folks!
Regarding which resort to chose, I agree with the "buy where you want to stay" idea, but I add a twist to that. I say "buy at the least expensive resort which you love, being perfectly happy staying there if nothing else is available at a non-home-resort". For example, we own two AKL contracts. We love it there. But sometimes we want to branch out and try other resorts. So, we will book our trip at AKL at the 11 month window. Then at the seven month window we will try to book the same dates at Poly, for example. If available we are golden. We cancel AKL and book Poly. If not, we might try Copper Creek. If we strike out everywhere, we are thrilled to be staying at AKL. It has a savanna, amazing theming, fantastic food, and we rent a car at Disney so we don't mind the lack of transportation. Win-win.
Hope this helps.