shipping charges question

Is there a way to do this in regards to shipping cost? (I have the basic software but I would be happy to upgrade.)

The first book you buy is a flat price of $5 for shipping. Every book thereafter (in the same shopping cart session) is another $1 each.

Yes that's possible.

Just set a weight of 1kg for all your products.

Then, create manual shipping methods like that:

from 0 to 1.5 kg => $5
from 1.5 to 2.5 kg => $6
from 2.5 to 3.5 kg => $7
from 3.5 to 4.5 kg => $8

...etc...