Booking Calendar

While a distribution is a great thing to aim for, it isn't happening today. In the mean time I feel that a good set of documentation describing how common tasks a BnB, or holiday home, website might want to achieve.
One of the biggest of these for a holiday home is a Booking Calendar so that people can see at a glance if the house is booked at any given date as well as the rate for that time.

I've been working with CCK, Views and the Calendar module and getting the calendar to show one type of content (a booking for example) was easy enough, but how to get it showing two types of content (season and bookings) is proving much more difficult, and a little searching around has shown that this has confused a few people. A good detailed How To on setting up something like this would be superb.

Now, this is the only area I have had difficulty with, what else have people found difficult to get working? If we can make it easier to set up this sort of website manually it'll make things better in the long run for a distribution!

Thanks for reading,

RandomCake