Yes, and the reason I added that caveate. It all depends on various factors including how much we travel, number of points earned and redeemed per year, source of points earned (self or employer - yes this IS a factor), single, couple or family, only being a few. For my current travel plans, if I were in the OP shoes paying $400 night for 4 nights would be the better option, but I am not and if it works for the OP then that is what counts.

I am doing SWP/Asia in Nov/Dec and have a choice of paying for 5 nights Sydney Harbour Marriott ($369 AUD/nt [$327.55 USD]) or 7 nights at Phukett Marriott (7885 baht/nt + 19.58% tax [$285 USD]). It would be 110000 pts for Sydney 5 nights, or 115000 for Phuket 7 nights. The kicker is all of Sydney Harbour Marriott award stays have a $ surcharge for Harbour/Opera House view, Exec floor, or Suite, the least of which is $80 AUD/nt, so it calculates out to the following: if I use points at Sydney I save $1283 or if I use points for Phuket I save $1995. I am using points for the less expensive property because the return is better. I also am using points for a week in Paris next May and a week at Vail in late March which are a much better return than either the Sydney or Phuket properties, so having enough points for Sydney is just not an option. If I were adding a $400 stay in NYC (where there was no standard award availability) to that schedule, then I would pay cash or pick a date when there was standard award availability if that was an option. Since I am single and don't have to take into account family member school and work schedules, I have that luxury. Of course if dates and reason for going to NYC was out of my control such as wedding, graduation, etc then that would not be an option.

As you can see from this example a lot of factors need to be taken into account when doing the math. Each person's situation is different, hence the suggestion of doing the math. As it is, in my case Phuket is getting very close to my lower limit on point usage based on its value at 1.7¢/pt (raising my own eyebrows). I think our need to maximize points is also based on the source of those points. If ones PAID stays are 90-100% paid by their employer it is much easier to rationalize using points for any and possibly all personal purposes. You folks are very lucky IMO. For those of us whose PAID stays are 90% personal out of pocket travel then there is much more pressure to maximize points to save net dollars spent out of our own pocket. Hence the reason for planning award and paid stays 11 months out, consistently watching room rates for specials and or rate drops, weigh paying for the $400 rooms and saving points ot use for the $800-1000 rooms.

In that light I should probably pay for both Sydney and Phuket, but my trip is already well into the 5 figures, so I am trying to minimize some costs; and saving $1995 for 115000 points isn't too bad.