You are making it way too complicated.
All the pages of discussion basically miss the very basic point - Honors has gone REVENUE-BASED program. And Hilton has assigned a fixed value range to their points, that the required points are directly tied to the room rates of the dates you want. It is just like how Southwest or JetBlue program works.
Just use the simple rule - the HH pts are now worth between $0.004 to $0.0055 in 95% of the case. The remaining 5% would be either an extremely poor below $0.004 value or a rare case above $0.007 value (happened to our upcoming stays in Poland at airport Hampton and HGI).
Gone are the days when one could get value close to $0.007 or above.
So use this as your yard stick on how much intrinsic "value" you would earn by your spend on the targeted cards then decide whether it is worth it or not to cumulate Hilton points.
For the majority of folks I would venture to say, it no longer makes any sense to purposely acquire Honors points because the intrinsic value is now at a very low $0.004 to $0.0055 range. This makes it even worse than IHG pts which traditionally has a low value but yet the chance of finding double of that in IHG program is now bigger especially in some European locations due to IHG still on a fixed point level chart.
Once the points have an assigned value by the program, almost all the arbitrage value is wiped out. It is just as simple as that. But we have to give it to Hilton to masquerade this as a big "enhancement" to now let you freely choose how many points to use....
