According to my local USPS PO you cannot do a delivery confirmation on an item shipped "Media Mail". Suprisingly the item I just received from hitmenow.com did indeed have both.

So what's the deal? Is my local PO wrong?

Your PO is wrong. In fact, it is more expensive to get delivery confirmation with media mail than priority mail (.50 versus .40) It is a way of encouraging people to do priority.

I went through this last week with the Post Office on a package I mailed. They said I could only get delivery confirmation on packages sent priority and parcel post. I ended up using priority to get delivery confirmation. But on back of the receipt they gave me says it is available for priority mail and package services (parcel post, bound printed matter, media mail, library) only.

Delivery confirmation is most definitely available for media mail, which is one of the "package services" mentioned above. Right on the delivery confirmation tag, you have to specify whether it's for priority or package services.
Also as mentioned, it is indeed 50 cents for confirmation on media instead of 40 cents on priority.

Unfortunately, delivery confirmation is not available for first class mail. Of course, as a clerk at the post office tole me, there's a good reason for that, because it would take a lot of business away from priority mail. People would use first class with delivery confirmation for packages that weighed just a few ounces (like a DVD). You'd get about the same delivery time at about half the cost.

I sent media mail with delivery confirmation with no problem.

Media Mail is considered a package service. Below is a quote from their website.

http://www.usps.com/shipping/packageservices.htm

I sent Media Mail w/ confirmation just today

I have run into a PO employee that said it wasn't available for Media Mail, but on the back of the delivery confirmation slip it clearly says "Media Mail"

As a postal window clerk, I know it's available. Unless you're in some little bitty town, they will probably be on POS (for "Point Of Sale", not ...). Once you select they type of mail you want (Priority, 1st class, Media...) it shows all the options for that class. Not only is Delivery Comfirmation an option, for the last few months, the computer should prompt them to specifically ask if you want it. A few POs are still on the old system that required you to know all the various permutations, but now the computer does it all for you.

As you've seen, we do in fact use D/C for Media Mail. Unfortunately, we can't use it for First Class, which is a bit of a issue for us...

FYI, I spoke with a senior clerk at my local PO in VA and she told me that the USPS intends to offer D/C on First Class packages in the next month or two. So you may want to inquire about this next time youre in your local office.

That's really good news and I'll ask about it. Maybe it will be timed with the new changes in postal rates, which I think is due in June.

Delivery confirmation is a joke because it really doesn't prove anything.

There's a page at www.usps.com that will allow you to create a FREE delivery confirmation label (for priority mail). Use this rather than paying. If you use the free label and the postal clerk says you have to pay, tell them to read the manual or contact head office. IT IS FREE

As mentioned, it's 40 and 50 cents for priority and package mail respectively. This is the "Retail" rate. If you use the USPS page for priority mail, it's FREE. If you use the shipping software (available for free from USPS), you can also use delivery confirmation for package services at a discount ( 12 cents I think). The free/reduced charge is known as "electronic rate'.

Remember, delivery confirmation doesn't prove anything really. If the postman delivered to the wrong house, it will show up as delivered. I've heard some post offices allow the driver to scan the package as delivered as they load them in their truck to be delivered rather than be scanned when it's delivered at a house.

It took me a while to find the link. Here it is a direct link to the page that jandaman is talking about:

http://www.usps.com/cgi-bin/api/shipping_label.htm

Where can this be found on the USPS site? I couldn't find it up there.

Nevermind I found it here:

http://www.uspswebtools.com/ShippingAssistant/

Does anyone know if you can pay for postage when creating mailing labels with the USPS Shopping Assistant without having to go to the Post Office?

You're right, delivery confirmation doesn't prove that the receiver actually received the package (not unless you do a signed receipt too), but it works pretty well, and usually establishes that the package at least made it to the appropriate post office.

I've had a number of occasions where it showed the package was delivered or returned to the PO and never actually made it. The USPS then actually allowed me to talk to the local post offices and the guys on that end know their routes so well that they can pretty much figure out the problem. It works.

Delivery Confirmation is important because IT is proof enough for paypal, billpoint, etc. It gives you cover in case someone says they didn't receive your package. Plus, you have some definitive proof that you sent it (as opposed to the receipt which only says zip code and not address)

Sorry, should have put direct links to make it easier.
If you have a real merchant account, the customer is always right so even signature confirmation is worthless as you never had the CC in your possession to do an imprint. Even for paypal, I don't think delivery confirmation is enough as it only shows the zipcode it was delivered to. Signature confirmation is acceptable I think although I may be wrong in regards to paypal's policy

Now, for those that hate standing in line and want to print out postage, there's 2 options I recommend.
Clickstamp from pitney bowes ( too lazy to find link) is $1.49/month and will allow you to print unlimited pieces of mail. This is a barebones package that only prints postage, no extras like delivery/signature confirmation.

The highly recommended by me and the sellers of ebay is Dazzle from www.endicia.com which is $9.95/month (or cheaper if paid for 1 year). This is a great software package that does it all, delivery/signature confirmation, insurance, etc
I take about 25 packages/trip to the post office and if I had to wait in line, I'd hang myself. All these stupid people with 10 packages who tie up the line while the clerk puts postage on the package. And these aren't joe shmoes but people sending out packages as part of their business.

The monthly price does not include the actual postage you use though.