Both saddles are the solid, great Stubbens that last forever with proper care. Both the Kerry and Siegfried put you in a great position and are very secure. Both have very strong trees.
For both saddles, you should get picture taken directly from the front and directly from the back so you can eyeball the tree straightness. On the Kerry, the one picture kind-of shows this, but it's at a slight angle, so hard to tell for sure. It looks straight. On both saddles, you need to ask for the condition of the padding inside the knee-rolls, and the condition of the flocking (is it hard or lumpy - then you need a reflock)
The Kerry. Nearside billets are good, so the offside ones are probably good as well. I'd get pics of the offside ones to be sure. The cracks in the leather on the panels isn't really very important. Those are pretty slight, and may just be a defect or the grain in the leather. If they don't go through the leather, just give a good conditioning, and they'll be fine.
The Siegfried: You need pics of the underside and both billet-sets.
The Kerry looks to be better cared-for.
What are the asking prices on these?
If you look on eBay
competed listing for the Siegfried (not so many Kerrys out there), you'll see they go for anywhere from $150-$500 depending on the condition and what someone happened to be willing to pay that day.