Given that the point of buying the extra points is to rent to cover dues, you’d never be paying those annual fees. Thus you wouldn’t add them to the investment account, as you’d never pay them either way (or, you spend $32500 for 250 extra points to rent out every year, or you invest the $32,500. Either way, you’re not outlying $1750 on annual dues for those $250 points).
Ah, that’s a good point. Taxes on the rental income weren’t factored into the equation. So if you assume 22% taxes, those extra 250 points will only cover $2925 of annual dues, leaving you with $575 owed each year. This changes the math. If you invest $32,500 and get 8% return with 22% tax bracket and withdraw only $2925 each year, you’d cover ALMOST 24 years of dues. Of course dues will continue to increase during this time, but I don’t have the time right now to try to figure out the real math on all of this.
Of course if you’re buying 500 SSR points and paying $130/point, you’ve overpaid to buy in.
[Edited to correct my mistake in the math above.

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