Does anyone else have trouble deciding under the new(ish) Hilton points system when it is best to use points vs cash. For example, tonight, the hotel room I booked was 28,000 points or a cash rate of 136 USD(inc. tax). I booked the cash rate and will get roughly 2500 points for the stay as a Diamond, an extra 2,000 points under the current promotion and about 1500 points over a regular credit card by using the Hilton Aspire Amex (14x per usd on Hilton stays). So $136 for a stay plus a return of 6000 points vs 28,000 points seems like a no brainer if you value the points at .5c. If you value them at .4 though it is a bit of a wash. Status qualification is not a factor for me.

I guess the reality is you should always always get at least .4c per Hilton point and often can get more if the hotel has reached its max points price or if you use the fifth night free. Therefore, in this case, paying cash does make sense since I am running low on points and points is at best just matching the cash rate at their lowest possible value.

Ultimately I just find this program harder to judge when points make sense vs cash over the other programs, am I alone? Any factors I am missing?