I have 1300 points at VGF, I rent out about 600 per year to offset my MF + AP fees. Which has worked so far - I have chosen to go through a broker to rent my points out - so I do lose about $3 a point but will get $15 per point, but then I do not have the headache of finding clients, people backing out, and the number of other bad things that could occur during one of these arrangements- as most times they are done 8-10 months in advance - essentially the brokers ensure I am paid regardless of what happens. To me it is an easy way to recoup some costs without a lot of work on my behalf - other than physically making the reservation for the renters.
steward715 advice around which clubs to target is solid - and there is a lot to think about beyond the initial price point - maintenance fees + expiration dates are key - and will influence how much you can net off of the rentals - not to mention if you declare the income on your taxes. If your sole purpose is to buy points to make money by renting them - there are a lot safer way to invest 60K plus over the long term. One thing to be clear - I doubt that the rental market will ever dry up - just make sure you are not dependent upon renting out points to pay your maintenance fees.