Not sure if I’ve gone crazy

I totally understand wanting to add a second contract with direct points. Once your resale contract closes, you will qualify for better pricing on direct contracts so that is a plus. You might also think about waiting until Lakeshore Lodge opens up in 2027 to buy a direct contract there.

The ability to access all resorts is desirable, but your resale contract can access most of the resorts. Once you have it, see how much the access actually bothers you. Personally, I don't want to stay at Cabins at Fort Wilderness, so the only ones I'm missing out on currently is Disneyland Hotel Villas and Riviera. I've been able to get stays at Boardwalk and Beach Club instead of Riviera, and at Grand Californian instead of Disneyland Hotel Villas. So, it's hasn't been a real loss to me... everyone will be different on that. The thing that draws me to a direct contract for my next purchase is the ability to get a discounted annual pass. So LSL may be what draws me into a direct purchase. I get the struggle... you are already getting addonitis!
 
There will always be direct points for sale. No hurry to buy. Also, you can buy Copper Creek or more Boulder Ridge direct from Disney if Wilderness is truly your favorite. That's what I would do.

Riviera is a great choice if you want to stay there and you think that 150 points will be enough. It does have the resale restriction so if you decide to sell it later, the buyer won't be able to use those points anywhere else. If you are just looking for direct points, Polynesian is the best buy right now if you don't mind staying there. If I were in your shoes, I would buy where I wanted to stay most of the time. All the sold out resorts have points available for sale or will have them if you are patient enough. If you don't care where you stay and you want the best bargain, Polynesian is best for now. If you can wait, maybe Lakeshore will be better. We have no idea about that, though
 














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