Hi Storas,
Firstly, as far as valuations are concerned the words estibot and accurate do not go together. Estibot is a great tool, the owner is actually a member here by the way, but all automated valuations are looked down upon as they do not take into account any of the human nuances that occur when a buyer is valueing a domain name.
Now ClintonSexScandal.com is a definate winner! What with good 'ol Bill' and Monica and now with Hilary and her personal assistant keeps being mentioned in the political blogs, this is a good one for re-sale. Because of this and the clarity of the domain name it has to be a minimum of $1k.
If I were you I would consider putting RSS feeds on a site, I am sure it would soon climb in the rankings, then look at selling banner and text advertising, etc..
Definately a better bet than the Obama domain.