You actually motivated me to check this service out. I've been meaning to do this for a while, and since I didn't want to clean, I figured now is as good a time as any!
For some reason UPSP doesn't offer first class mail on their website.You have to purchase it threw something like Stamps.com, Or use Paypal and print out a shipping label OR go to the post office.
I just use paypal, it is really easy and just deducts the shipping cost from your paypal balance. It is usually cheaper than going to the post office and you get free delivery confirmation.
GoTo's right- when shipping prices went up, delivery confirmation was added to first class as a free service. You get delivery confirmation on all first class now, even if you don't want it :)
I logged in and logged out 12 times on Paypal and don't see anywhere for the multi order option. I got it figure out though doing 1 at a time, had 8 orders lol. To give an idea how much I saved on Paypal vs post office. I paid almost $3 for a 4 oz first class package with delivery confirmation and was $1.81 on Paypal. Talk about money savings! Thank you for all the responses and hope it brings a little light for those that didn't know about this.