fishnfly, you certainly have a lot of questions in one post. You may find it hard to get good responses here with all those questions. I will try to answer a few questions.
First, spend some time up on the stickys. There is a lot of good info there. The second link there links you (eventually) to Blonde Bomber's website with a list of Hilton properties by category
http://members.shaw.ca/deercroft/download.html That is one great resource. Check it out.
Second, with 200,000 points and diamond status, you are eligible for VIP awards
http://hhonors1.hilton.com/en_US/hh/...POnly/index.do . Seems to me you might have 11 nights or so depending on the category of hotel you choose. Unless you are using the diamond force, you should be able to get two rooms for you and your father. You can start by looking at availability online once you have chosen where you want to go. There are plenty of threads asking "Where is the best place to use points?" or "Where is the best beach peoperty?". Will you get the trip of a lifetime on those points and certs? Probably not but you could have just about a week in Hawaii or Europe (or many other places) with some creativity.
Best of luck.