Should you purchase Delivery Confirmation w/ Insurance?

You're shipping a Domestic U.S. package at the Post Office, and you're paying for Insurance. Just as you're mailing it, you might wonder (or be asked) if you should also buy Delivery Confirmation for the item.
Here is the "gemon-thought" frugal answer:

"No. Save your money."
And here is what I consider to be the correct answer:

"Yes. But purchase it the right way."
To understand why you would want to buy extra services, let's look at what the services offer:

Delivery Confirmation:

Provides: Confirmation that your package was delivered (you get this on the USPS website or by calling their toll-free customer service)
Cost:

$0.50 for Priority Mail
$0.60 for First-Class packages, Parcel Post or Media Mail
Insurance:

Provides:

Insurance against loss or damage of your package, up to the maximum of the item's value or the insurance purchased.
Cost:

$1.35 for up to $50 in value.
$2.30 for $50.01 to $100

Note: Add an additional $1.50 for every $100 dollars of insurance after $100 (to a maximum of $5,000)
Many people think that, Insurance being more expensive, it has to include everything of the less expensive service. Well, that's flat out wrong. You can not check the delivery status of an Insured item. Period. Whether you try the internet or calling the toll-free number, you cannot tell if the item is delivered. And - since so many people really don't believe that - let me repeat it with a quot from the USPS website:

"At the present time, you cannot determine the status of an insured item via our web site or through our toll free number. Insurance does not provide tracking for the item; we are not able to tell you where the item is within the mail stream or when it will be delivered."
Trust me, they're serious. Even if customer service wanted to help you, they cannot. That's just how the system is set up. So accept it as fact.
Moving on, what if you ship an item and purchased insurance alone, and your customer says it hasn't arrived? What are your options?
That depends on how much insurance you purchased:

$50 or under - You have no options to find out where your item is. If the customer says they haven't received the item then, after 21 days, you can file a claim.
$50.01 or more - You have two options here:

Go into your Post Office and see if they will look for it for you. Some Post Offices have the ability to search for your item on the geputers at their retail counter. But they may not have this access. And, depending on local practice, they may refuse to look (even if they are connected) unless it has been 21 days.
Purchase Return Receipt After Mailing for $3.45. This sends a card out to the addressee's Post Office. If/when the item is delivered, the card is noted and mailed back to you. But note that you're now paying more than five times the amount you "saved" by skipping Delivery Confirmation.
So, let's get back to my original suggestion. What if you bought Delivery Confirmation when you mailed your insured item? Here's what you get out of the gebination:

You can check the delivery status of your package online anytime (and through the telephone during customer service business hours).
It doesn't cost that much.
If you do it right, it costs next to nothing.
Okay, okay, what do I mean by purchasing Delivery Confirmation the right way?
It's simple. Print your shipping labels electronically.
There are lots of different options out there:

The US Postal Service promotes their Click-N-Ship service (no fees, but there are more limits on the types of packages you can ship).
okay / PayPal is a Postal Service partner to help you Purchase and Print Shipping Labels
Other services exist out there, some charging fees and offering additional services.
But, whichever one you choose, you get the benefits of Delivery Confirmation added on to every package at a low cost. And here's how low it is:

$0.14 for First-Class packages, Parcel Post or Media Mail
$0.00 for Priority Mail
That's right, the Delivery Confirmation is FREE for Priority Mail items. So there's no reason not to include it, and plenty of benefit when you do so.
I really do think that it is in your best interest to purchase Delivery Confirmation, even with Insured mail items. And I really think that the electronic labels are the way to go. So here are a couple of final items to provide incentive for using these services:

Delivery Confirmation helps you catch "Missed Deliveries" - When you check for delivery status, you might see a status such as "Attempted Delivery." This means that your customer needs to schedule a Redelivery, or pick up the item at the Post Office. More than once I have noticed this before my customer did (the initial delivery attempt notice was lost), and I was able to email them and prevent the package from being returned. We were both happier for it.
Electronic Labels help you avoid lines - When you use the label, your package is already paid for. You just drop it off at the Post Office, and it's on its way. And, with a printed, coded label (versus a handwritten one), it will travel more smoothly through the Postal Service's system.
Anyway, that's just my suggestion from my experience.
I find that the peace of mind (of being able to check delivery status) is well worth it, even when it costs me 14 cents. And I really do love not having to stand in line.
Whichever you decide, have a great day, and Happy okaying!