I'm just into manual gearboxes for the road any more dude, can't be arsed with a clutch when most of my driving is monotony; especially as i'm lucky enough to be able to race, i don't go out for weekend drives or anything like that.
The Tiptronic in the 997 is more advanced than the 996, but i've never tried the older car with a Tip gearbox. Only 996s that interest me are the 4S and the GT3 (Mk2), in manual to be fair.
The CSL is a completely different car, it is not that quick in a straighline but sounds sensational and feels like a quasi-race car. But at the same time its something to get precious about, with the easy to damage carbon and alcantara. Parts are also hard to get and expensive. There are also some reliability issues, but then again the 996 range is much worse for that (GT2/3 and Turbo excluded). I would rather a CSL than a 996, personally unless the Porsche was in fantastic condition.