I finally booked our flights to Puerto Rico for next February break! We're going to San Juan Feb 17-22. I used 109,544 UR points for 4 roundtrip tickets on Jet Blue ($1,643 cash price). I've been watching the prices for a while and $410 per person RT was the lowest I've seen, so I just went ahead and booked it.
For the hotel, I'm using 185,000 Marriott points for 5 nights at the Marriott on Condado beach. It would've been 160,000 but I'm using an extra 15,000 to upgrade to an ocean view room. We've never stayed at a beach resort like this and I figure what's the sense in staying on the beach if you don't have an ocean view, right?
Total cash price for the same room/same dates would be $3,308! There's a $30/night resort fee on points bookings (on cash stays it's 18%!) but I'll use the CSR travel credit (or SPG Lux credit if one of us ends up getting that card) to cover it.
I have to say, this hobby is addicting. I started out just trying to cover the cost of a hotel stay so we could fit a trip to visit my wife's family into the budget, and now two years later I'm booking trips for my family that I'd never be able to afford without using points to cover the majority of the cost. We live on a single income in an expensive city, and it's freeing to still be able to travel and give my kids these experiences. I still think one of the best things my parents ever did for me was scrape together the money to send me on a tour of the British Isles that one of my teachers arranged the summer after my 7th grade year. It was my first time traveling beyond the beach or Disney World, and I credit that experience with giving me the travel bug. Now I want to raise my own kids to be travelers.