The only way to print out postage for these type envelopes, that I know of, is through click-n-ship for business. It's a download that you get from USPS (off to right of the print labels page) and it allows you to do first class parcel which is what these mailers are considered. You can put in the weight just like a package. I may use it this year to save on waiting in line at the PO (except on the international ones). I was just playing around with it and it looks like the base price for mailing one of these is $1.95. You would either have to buy shipping labels to print them out on or print on regular paper and tape it on (uses too much tape for me). I'm not sure how the parcel labels print out as I have never done so. I buy the labels from labeluniverse.com, 500 sheets (1000 labels if you don't print receipt on the second one) for $57
I like to include the delivery confirmation on anything I send because there have been many times I get an email wanting to know where the package is and it had already been delivered. Some of the buyers that buy a lot on the LA print out their invoices and as the orders come in they take them out of the pile. Well some get in a hurry then forget to remove to invoice from the "has not been delivered" pile. This way I can say it was delivered on this date at this time.