Obviously it depends on your travel patterns.

But since most of us don't have our full travel plans figured out for a year in advance, it becomes a risk/reward question. If you travel much, it seems likely that you'll be able to get more than $95 from it. A $200 room night would be over $100 of extra value. But don't focus just on the upside.

If you can't use it at all, anywhere, then your loss is $95 (assuming you don't get any other value from the credit card). But there's also a scenario where rather than letting it expire, you end up using it for a cat 2 or 3 hotel that has a paid rate of $75. While you wouldn't want to keep the card knowing that's how you'd be redeeming, in this case, you're limiting your loss to just $20. If half the years you can use it at $150, and the other half only at $75, on average you're still coming out ahead.