I seriously thought about doing this about 3 years ago. In doing my research, I found that one property (I think Monarch on HH) would trade every year for 130K points. Off weeks sold for about $16K at that time. Current yearly fees are about $700/yr.

At that time Marriott still had the 425K Mile award (which I requested many times) and used the miles to go onto United. Four tickets anywhere yielded 240K Miles. You could redeposit the hotel portions of the award for something like 112.5K each, and net the miles for just 200K Marriott miles. Of course, you can even buy some of the miles for only 0.01/mile and that's not bad converting to Airline miles.

Now the equation is not quite as good. You can get 7 day stays plus 120K miles for between 235-270K Marriott rewards points. You can return the hotel stays for a credit of 45K- 55K MRP if you want (assuming they still allow this ...).

So, two weeks would just about equal one award. You'd have to invest about $32K on the timeshare (if you're a good, you should be able to put this on your credit card and get more points), and then pay about $1400/year in fees plus $104x2 to exchange into points.

Value of the award depends on how you view it, but a cat 7 stay at the Paris Marriott is hard to get less than $400 a day, which is a value of $2800. 120K miles is worth what you value them for, but if you regularly buy business class tickets, this could be worth much more then the "standard" $0.025/mile most people use.

Say you wanted a million miles a YEAR to use as you wanted. You'd need about 8 235K awards minimum (yielding 960K miles). 15 Weeks would be enough. That would cost you about $240K plus $12K/year in fees. In return, you'd get 1M FF miles on any airline per year (until they change the program again - which is what prevented me from doing it) and 15 weeks in a cat 1-5 hotel (which you could turn back in for more marriott reward miles - something like 700 K more).

For this, you get enough airline miles to get 10 first class ticket per year to Europe (Assuming you can find them), which could cost you $4K - $8K per ticket. Again, you have to do the math for your specific FF mileage usage.

So simple math (not wanting to do a DCF) You could net about $40K - $12K year = $28K or >>12% annual return on your $240K investment AND have a residual basis on your investment of at least 75% of what you paid for the weeks. Like I said, you'd really have to sharpen your pencil to make sure this is good.

The flexibility of being able to use the actual weeks, trade them for points, trade the for weeks elsewhere and even to sell the timeshare all have value, which realistically would need to be entered into consideration.

Of course, all this assumes that the Monarch deal is still around and that you can re-deposit unused hotel stays at some credit.

Billy