I am looking for what people's thoughts to this are. Do you treat this like stocks and actual Real Estate or are you in it for the looks. Do you just look at the domains or do you look at the whole picture?
It should be like stocks and real estate. If you own a sizable number of domains (I've got over 400 in my coffers) you start analyzing how much each is worth, which events could influence its worth, how much it could be worth if you do something with it, and finally how much you could realistically sell it for (since the worth and sales price are more often than not quite different). I treat online property just like I would treat real-life property. Since I know that in worst case scenario (god forbid *knocking on wood* my business goes bust, health problems, emergencies, etc...) I can count on X amount of money to pull me through the hard times from selling my property. If I don't know what it's worth, it won't be of much help since I will either undersell or ask for an unrealistic price and therefore would be stuck.
There are a lot of factors involved in a sale. Some buyers are looking for sites with established content and members, a mailing list, etc.. Other buyers are looking for a site with a lot of backlinks and Google pagerank to use to increase other sites they own's search engine rankings. Other times somebody will buy up smaller sites in their niche to keep all the traffic coming towards them. There are many factors involved.