[cubsguy1969]

Can you purchase media mail postage through paypal? I've never tried buying postage in any capacity through paypal or ebay.
I know that the automated machines at the post office won't work with media mail. You have to take them up to the counter and have a real live human do it for you.

Edited to add:
I usually insure pricier items and eat the cost, just for the peace of mind. But I sell lots of books and such for $6 to $10. Seems silly to me to pay for tracking on every one of those. I'd rather risk the occasional package getting lost or a buyer "claiming" he never got the item and have to refund the 10 bucks. I think I come out ahead. I've found that most book buyers seem to be fairly reasonable people. Maybe not as many crooks as on the card/memorabilia side of things. But maybe I've just been lucky.