If that Chile stamp has no faults (e.g., thins at the back, glued hinge), then half price from a brick-and-mortar dealer is not a bad price. If you want to sell it, you would be lucky to get $ 5 for it. There is nothing wrong paying something extra over what you would pay on
ebay. A dealer may have knowledge and identify genuine from forged stamps, detect faults, built a relationship and take a stamp back when it turns out to not be what it was sold for. That is worth something, especially if you see this as a hobby.
Unfortunately, from what you have shown, your dealer is happy to sell everything at half catalogue price, even if it is heavily damaged.
As for your Penny Red. There are many. If unchecked, you might end up with a rare plate. In general, however, unless the stamp has four good margins, looks fresh, and has a light, neat cancellation that is correct for the time of use, its value drops of a cliff. If the image is cut into, it is one of millions available and worth only a few dollars.
Penny reds can be bought in quantities for a few dollars.
Even worse is the case with the Penny Black. It is a very common stamp, just not in superb condition. At auction, superb examples sometimes make as much as 75 - 90% of catalogue. Usually, the cancellation adds something at that price. If the image is cut into and it has an ugly, smudgy cancellation (unless it is from plate 10 or 11), it will not be worth more than $ 50. And if it hardly has any margin, you can get them for $10.
As someone wrote above: run away from this dealer. He is selling you defective stamps at dealer prices that would be fair for fine stamps. And even then, you should realise a good dealer will be more expensive than
ebay and the likes, or an auction.