This is a tl;dr sparked from a conversation with a good friend regarding management of personal photo libraries.

In this modern era where it's not unusual to take dozens of digital photos per day, it helps to have a system in place organize your files.

First of all, you've got to be able to find particular things when you go looking for it. If you have a lot of photos and videos it's easy to get lost or spend a long time browsing a huge list where you might miss something.

Another important factor is backup. You must have a backup system or you'll inevitably lose some of your files.

Backup and import both share a common factor: they must be automatic. If they aren't, you are human and you'll slip from the routine losing the benefit.

Directory Structure

For me, the key is a directory structure that I maintain. Here's how I make it easy to both use and keep up with. I have a Pictures directory in my home directory on all my machines. When I drop photos in I always organize everything by the year and month. I find chronological order to be the best overall sorting method. This leads to a flat directory structure that's easy to use.

Pictures
├── 2014-11
├── 2014-12
└── 2015-01

Some cases arise where a bunch of photos correspond to an event that I want to make note of. Coming up this June I'll be going to an airboat rodeo. When I drop the pictures from that event into my phone my new directory structure might look like this. Notice that I've maintained the chronological ordering and tagged a directory with the event. There is still a 2015-06 directory, but the 2015-06-airboat-rodeo directory is where I moved those pictures that were from a particular event I wanted to segregate.

Pictures
├── 2014-11
├── 2014-12
├── 2015-01
├── 2015-02
├── 2015-03
├── 2015-04
├── 2015-05
├── 2015-06
└── 2015-06-airboat-rodeo

As a Mac OS user, I could use the OS's built-in tagging system. The problem is that some of my time is spent on Linux or Windows where I'd lose access to those tags. I have other reasons that I'll get to shortly as well.

Dropbox

Now it's a good time to just come right out with my opinion. I believe [Dropbox][2] is the best way to sync your pictures into the cloud.

Simply put, Dropbox is everything you need, and nothing you don't. There's almost no chance that Dropbox will introduce a feature next week that, for example, accidentally posts your pictures to a public view. This is a direct criticism of Google and Yahoo!'s photo storage options. Some people want that social aspect. I don't.

It's critical to use something to sync the pictures to the cloud. A lot of us are using more than one computer on a regular basis. Cloud sync takes the gymnastics out of that process. Computer hardware is also imperfect and prone to failure. Cloud backup gives a recovery option.

Speaking of recovery options, it's good to have more than one backup system. For me, I can restore my pictures from Dropbox, but my whole computer, including the Dropbox directory, is also backed up into my Drobo 5N using Time Machine.

iPhone and Other Devices

Most of the time my pictures are taken from my iPhone, but I also have a camera that stores pictures on an SD card. In either case, Dropbox has a great feature. With the Dropbox app installed on your computer it will offer to import your photos into a Camera Uploads directory when you plug in your phone or SD card. This is a step where automation is critical. If you have to manually import your pictures – let's be realistic – you are going to forget and leave the pictures poised precariously on a device that you are likely to lose or break.

The Camera Uploads directory is in your Dropbox, so the pictures are being synced into the cloud from the moment you plug in your phone or storage device. It serves as a great holding area to keep photos until you move them over. The photos will be renamed from the native nomenclature and organized by the date when they were taken. This is perfect for making the process of moving photos into the aforementioned chronological directory structure.

It's worth noting that this Dropbox upload procedure also works for videos which I usually keep in with my pictures.

Camera\ Uploads
├── 2014-11-01\ 12.00.38\ HDR.jpg
├── 2014-11-01\ 12.00.38.jpg
├── 2014-11-01\ 12.58.12.jpg
├── 2014-11-01\ 16.57.44.png
├── 2014-11-01\ 17.22.16.jpg
└── 2014-11-03\ 08.04.23.mov

Photo Management Software

I don't personally find the need to add any photo management software to the equation. Mac OS gives me the tools I need through Finder. That said, I do see the need in general and I keep an option installed in case I decide to use it. I go with Google Picasa. The reason is because it doesn't enforce a particular directory structure on you. It does some nice things if you want to be able to tweak your photos and restore the original. It has the advantage of working on both Mac OS and Windows if you are switching platforms.

There are other good options when selecting photo management software and whether they are truly "good" depends upon your needs. The one I do suggest avoiding at all costs is iPhoto. It is the most restrictive as far as directory structure. Apple is replacing iPhoto with an upcoming release of Photo, but I haven't looked into whether it's an improvement.

Pictures In Dropbox

My last piece of advice is a bit more technical, but in Mac OS I like to simultaneously use the home Pictures directory and have it synced in the Dropbox. I accomplish this by creating a [symbolic link][ln]. Think of a symbolic link as an alias. The original directory is a normal directory, a symbolic link is that same directory in every way with its only difference being that it exists in a different location in your directory tree. This allows me to have a directory that exists outside Dropbox but is still synced as if it were inside.

When I set up my computer I link my home Pictures directory to my directory in Dropbox. If you use this terminal command, make sure Pictures is empty in the home directory first. Otherwise, you'll erase your Pictures directory.

ln -sf ~/Dropbox/Pictures/ ~/Pictures/