I like the idea of having him pick up the hotel tab next year. Is that an option?

I've gone on trips with friends where I've expected them to pay half. I've been stiffed a few times and have actually lost friendships over it. I since decided that if I was going to invite someone on a trip, I would just pay for everything and whatever the friend decides to give me back is great. Without the expectation of getting anything back makes things a lot more easy-going.

Since I travel often, I'm able to typically stay at a lot nicer places than most of my friends would. I certainly would not expect your friend to pay half of the $300 cost. If you want do exchange some money this year I would base it only on the amount of money that you would have paid. Hopefully your friend would offer to do something above and beyond but if your friends are like some of mine then they might not have the financial ability to give you much.

Thinking about this a little more I might consider telling your friend that you're able to stay at a much nicer hotel that is going for about $300/night but you were able to get a deal at $150/night. He doesn't really need to know how you paid for it. In all reality you are paying quite a bit for the rooms even though you're using points.

Let us know what you decide to do. I'm really curious if there would be a better way for me to manage my own travels with friends.