Find a best cash price, priceline or whatever, for a few typical stays you would have.

Then find the cheapest property on points (or points plus cash) that would work for each of those stays, in each program.

Divide the net cash cost by how many points you need, across all of those typical stays.

Will give you a typical value for a point in each program, for your travel patterns.

Then when you book, use that average value as a reference to determine which program (or cash) is the best value in that particular situation.

For example: If I typically get 1/4 cent value from a Hilton point and 2 cents value from an SPG point, and I have the choice of 25000 Hilton points, 5000 SPG points, or $85 cash on PL for a stay, I would calculate:

$62.50 vs. $100 vs. $85, and use Hilton points.

My Philosophy: Most points don't pay dividends. Many investments do. Keep your cash in the market and churn & burn as far as miles go, as long as you're redeeming somewhere near the median redemption value.

I only avoid using points when I want to choose a different hotel for convenience or if I'm at a conference/event related to a sole proprietorship, which is a business expense. If there is any possible way to use points, I will, unless it is a business expense, out of convenience, or the redemption value is absolutely terrible (well below the median value).

Likewise, if I can get a direct flight on Allegiant for $150 RT vs. 25,000 in miles, it's a no-brainer. I would never like to use airline miles for less than 1 cpm when compared with a reasonable cash alternative, but I'll redeem all day long at 1.5+ cpm to take kids to Disney Parks. Doing so really helps us afford trips we might not otherwise be able to take at this stage in our family life and careers.

I, too, recognize that I am in the minority, but I frankly would rather be able to take the family on vacations AND fully fund our IRAs than to stockpile points for a trip I'm not likely to take until 10-20 years in the future. By then, I may just snag a deal on TravelZoo and pay cash (assuming the Zoo is still around).

I agree with LowFlyOver, earn 'em and burn 'em.

I travel enough so that I have plenty of miles for "emergencies", or for situations when I need/want to go somewhere and the cost of the last minute ticket makes it hard to rationalize the ticket. On the flipside it is also hard to rationalize paying, for say a $100 Holiday Inn room somewhere when you can get the room for 10,000 points and you have enough points to get any award they offer, and you generate a lot of points every year. There are a lot more things I can do with $100 cash in my pocket vs 10,000 hotel points.

I also use points for magazines, which some people think is insane. However it seems very rational to use 1,000 points or miles for a subscription that you want and the lowest cost you have found for the magazine is $50. When you realize you will get twice those numbers of points on your next round trip ticket it really doesn't take to much thinking.

Like money, the more points/miles, you have coupled with the more you earn every year tends to make you value them less than the person who might have less. A higher level elite flyer isn't going to value an upgrade award as high as someone who travels infrequently and received most of their points through a credit card.

There are too many variables and the perceived value of the points/miles by people to have a concrete value structure. It isn't money, and although unlikely the programs could go away. Also like money, the points don't have any real value to you until you use them.

I agree with LowFlyOver as well. The downside is I'm sitting on enough miles where the wife and I can fly J wherever we want for the next four years... we're planning on one nice trip a year. I'd rather do that than waste miles just to get rid of them. But I'm not saving them for retirement either.

When it comes to hotel points and using them for free nights as a rough estimate...each hotel chain has a aslighly different formula...

for Marriott I see 10,000 pts= $100. I have no problem using 10K pts for a hotel rate of $150 or higher. I wouldnt use 20K points for a hotel that I can get a room for $85/night

With best western and Choice I look at 16,000 pts = $100.

There are seasonal bargains at some lower tier hotels. Mardi Gras in New Orleans, summer at the beach, Jan/Feb in south Florida, etc.

Last year we stayed at a great Holiday Inn beachfront during summer in Ocean City, Md. for about 5K PC pts + $50 night. Rooms were running $300/night.

Hard to get sometimes but a bargain if you can.