My comments for what they are worth given the level of personal taste in such a lovely purchase. The warranty/age/mileage/paperwork would influence me as lot as well. Timeless is the Aston pre-owned brand so I am guessing that car has a solid warranty which is worth it unless you have every bit of paper and can check out the previous owners or know the dealer well.
I like the alloys on the first one. They contrast and set the car off well.
The second one looks like it has had the wheels changed for a more modern design which I am not as keen on when put on the cleaner DB9 shape.
Normally I like either dark with light interior (three) or dark/dark (one) but I have to say the lighter colour does show the curves better in the photos and possibly real life.
All nice, lovely choice of car.