We have a three month old kid. That means we take a lot of photos. I've done the math, and in the last three months we've taken 1,202 photos of him. As I'll write about in my upcoming book on Dropbox photography, all of those photos are stored and sorted in a shared Dropbox folder that both my wife and I have access to. For other family members and friends, we share the best of those photos via a shared iOS Photostream. I'm really a big fan of this feature. With just a few taps I can share as many photos as I want and have them near-instantly delivered to the twelve people who subscribe to our photostream. Everyone in our family and circle of friends has an iOS device, so no one's left out. I never have to fumble with emailing attachments, or posting links to Flickr. All the photos are available in the native iOS Photos app. Best of all, I can post comments with the photos I add, other people can like and add their own comments, and they can even share their own photos, too. It all works splendidly.

The only downside is for our grandparents. They don't have iDevices. Sure, our parents are always showing photos to them on their phones and iPads, but our grandparents miss out on the personal connection they'd get from having their own collection of photos. To try and fix this, I've started physically printing and mailing batches of photos to them every ten days or so. They love getting photos they can touch and display in the mail. It really is like their own real-world photostream.

The problem is this is manually intensive. Printing batches of photos, keeping up with ink and photo paper, finding sturdy enough envelopes to handle twenty photos at a time, and then dealing with postage slows the whole process down. So I've been experimenting with three online photo delivery services to handle all of this for me.

Over the last few months I've tested Shutterfly, iPhoto, and PicPlum. Ideally, I'm looking for a service that I can quickly upload the latest photos - from both mine and my wife's iPhone and from our good camera - and have them sent to multiple addresses without having to re-type the address each time. The photos need to be delivered fairly quickly and, most importantly, arrive in good condition.

I've given each of the above services multiple tries, and they all have their good and bad points. For those of you who like to skip ahead, the winner was Shutterfly, followed by PicPlum, and then iPhoto.

iPhoto

I really wanted to like iPhoto, as it's Apple's recommended service. But there are a few negatives that keep me from going this route. First of all, the iPhoto iPhone app is nearly impossible to figure out. I'm an app developer by trade, so I like to think I can understand most apps without much instruction, but the iPhoto UI baffles me. Selecting multiple photos and preparing an order for delivery was a beast of a process. Add to that extraordinarily long ship times and they were a clear no go. The actual photos were of middle of the road quality and arrived in a plain white cardboard envelope that seemed to protect them well enough.

PicPlum

PicPlum is an interesting service. Unlike iPhoto and Shutterfly, which are really designed for printing and delivering photos to yourself, PicPlum bills itself as a service designed for printing and mailing photos for other people. Everything is done through their lovely web interface. You can drag and drop your photos directly into the web browser. Then it's just a matter of choosing the recipients from your previously saved addresses.

PicPlum loses points for not having an iOS app. Typically, I want to only send my best photos to be printed. All of the best ones are already handily organized and available in our shared photostream. If they had an iOS app, I could choose them directly from that album. But, as they only support desktop uploading, I have to find and gather them from the various photo albums in my Dropbox. This isn't a huge deal-breaker, but it is slightly less convenient.

The biggest downside to PicPlum, and ultimately the reason I no longer use them, is the photos arrive in a flimsy paper envelope. The kind of thing you'd mail a birthday card in. I used PicPlum to send twenty photos three times. Twice, the envelope arrived torn with the photos sticking out. In one case, the adhesive sealing the envelope was barely affixed and everything was in danger of spilling out. And while I didn't encounter this problem in my testing, with such a flimsy delivery method, there's absolutely no protection against water damage.

I'm actually quite sad that I can't use PicPlum. They make it easy to send to multiple recipients and their photos were by far the highest quality of the three services.

Shutterfly

As I said above, Shutterfly is who I decided to go with. Their iOS app is a little long in the tooth, but it's serviceable and easy enough to use. I'm able to choose photos from my Photostream and upload them quickly. I can pick from a list of previously saved addresses. The price is the cheapest of the three services, and the photo quality is good. Unlike PicPlum, Shutterfly's prints arrive in a sturdy cardboard envelope inside an even larger cardboard sleeve. I've mailed six batches of photos so far and none have arrived damaged. The double envelopes even protected the photos against our rain soaked mailbox.

The only problem I've encountered with Shutterfly is their shipping time. Using their default shipping option, which is about three dollars, the photos arrive anywhere from five to twelve days later. For three bucks, I'm not sure what I expect, but two weeks is way too long to wait for a delivery. So I usually just pony up the extra cash and pay for the $10 two-day delivery method instead. It's faster, and comes with a tracking number, too.

Overall, our grandparents have been thrilled with the service. They absolutely love getting their bi-weekly photo surprise in the mail. The physicality of holding real photos in your hands makes them feel connected to our son in a way that FaceTime and flipping through photos on an iPad just can't. I highly recommend keeping your non-technical friends and family in the loop this way.