First of all I'm new to Starwood so hopefully my questions aren't too stupid/redundant.

I currently have ~14,000 points. I have my trip planned for the first couple of weeks in December. I'm arriving and leaving from Frankfurt. There will just myself and my friend.

My itinerary is still up in the air as I'm trying to work out a nice loop/path to/from Frankfurt. I'm pretty sure I will be in Munich for 3 nights and Salzburg 2 nights. In my scanning of some of the threads here I see that both cities have properties you can use your points for.

My questions are:
1. I'm guessing at that time of the year the 50% of rack rate is probably not very useful, is it?

2. Some of the cash+points availability seem more interesting. Is there some kind of value most people here assign to points? How do you generally figure if it is a good deal?

3. When would you consider using all points for a free night?

I'm generally looking for hotels reasonably close to public transportation since we will not have a car and being wintertime we'd rather not walk too far. I have browsed through some of the threads on specific properties in those areas.

Thanks for any help.