I am a saver of points and miles and have set very lofty seven digit goals for our retirement. Fortunately for us, we are very much on track to hit those goals.
Having said that, we have also had some wonderful free trips:
Two Concorde tickets in exchange for 100,000 Starwood AMEX points. Value $24,000.00
Four premium BA tickets from Seattle to London, Malaga, Barcenlona, Palma, London, and back to Seattle, using AS miles. Value $60,000.00 ^
Five last minute NWA coach

(this was before FlyerTalk) tickets, Seattle to Sarasota, to attend my mother's funeral. Value $10,000.00. That seemed like a very big deal to me back in my Pre-FT days.
We have also used points to score some pretty pricey hotel rooms, especially when attending mega trade shows in Europe where we have seen the rates climb to over $750.00 per night for a plain vanilla room.
Like,
Randy, I have considered that, if it were every necessary, I could spend many months in a classy hotel for free. Hopefully, however, I will just keep earning until I retire and then blow them all flying all around the world, loving the high life.