Originally Posted by ORD-TGU

This is very creative, if you value points that high, go for it.
As a reference, you can buy directly from Hilton at $.01 per point.
I value at half of that.
You can also apply for a couple credit cards that are fee free and and get the same 100K for no out of pocket expense (just credit pulls)

Or if you spend that $737.50 on actual stays at Hiltons on relaxing vacations, pay using the surpass and having gold status plus the current 3x Weekend promo plus my way, Amex booking bonus, GG 40% sale, Gold bonus, etc, you will end up with around 50K and have plenty of nice memories of your stays. (plus th current Surpass 50K sign up promo if you dont have it)