One of the most difficult work flows I've had to work out over the last couple of years has been that of photo management. I've had other work flows such as managing tasks that were difficult to implement; mostly because I don't stick to the work flow my self. Photos however has always proved a difficult task to solve.
I've come up with a solid solution that works really well. It allows me to have all of my photos & HD videos from my camera to both my Mac and my iPhone. The big plus is it takes zero storage on my phone.
You're out with family at a birthday party and take a lot of pictures. You get home and your to tired to pull the photos off, so you postpone it. Before you know it you have 400 photos on your device over several weeks. Then the unthinkable happens - you drop your phone in the sink or loose it at the mall. Photos and videos are now gone. Sure you can retrieve them from iCloud backups, if you have that set up and if you have less than 5gb of photos and videos. What now? You've essentially lost them.
Another scenario is one of you doing a great job maintaining your library. Everything is tagged and filed in a very organized manor. The issue is that your library is 200gb and you can't fit that on your device. I don't know about you, but we take nearly 4gb of photos and videos every month. I can't fit that all on my device.
Solving the problem
Solving the problem requires several things. First, we need to eliminate the need for syncing. The fewer steps needed to back up the photos and provide access from anywhere the better. The second issue that we need to solve for is providing access to all of the content to our devices while we are not at home.
Syncing photos can be completely automated across both Windows and OS X. We do this by setting up Photo Stream on our devices and our computers. Photo Stream will automatically sync your full resolution photos to your computer. No need to plug in a cable. While your device can only hold 1,000 compressed and resolution shrunk photos in your Photo Stream, your computer will hold every single photo until you run out of disk space, at full resolution. So this solves the need to sync your phone in order to get them off your device for the most part. The only thing you will still have to plug the phone into the computer for is pulling off the videos. You can always use Dropbox as an intermediate solution for this however, buy letting Dropbox auto-upload the videos you can then just import them into your library easily.
Next we need to tackle getting the photos made available to your devices even if you don't have room for them. We can do this with a free Flickr account. Flickr offers users 1TB (1,000GB) of storage for photo's and video. You can upload a maximum photo size of 200MB and a maximum video size of 1GB. The maximum video length is limited to 3 minutes at the time being, so keep that in mind while recording videos. It's best to record them in short pieces. Otherwise you will need to split them up in iMovie or something on your iOS device.
The Flickr iOS app has a Auto-Upload feature. Any photo or video you take on your device will be automatically uploaded to a "Auto-Upload" Set (Flickr version of Albums). You can then organize the photo's from your device or from your computer within the web browser however ever you want them to be.
Using Photo Stream and Flickr for wireless syncing of your pictures and videos, provides you with a easy method to get your photo's on your computers without any cables and shared on all devices without taking up storage space.
Organizing on your computer
I used to maintain my photo's within iPhoto, but have since migrated to Aperture. I'm actually looking at moving to Adobe's Lightroom so I can use it cross-platform on my Windows partition and my OS X partition. I have also used Google's Picasa as well and find that regardless of the software you use to manage your photo library, the following organizational system can be applied to them all.
Start by storing all of your photo's in a heirarchial fashion. You place your photo's into a folder (or project in iPhoto/Aperture) based on the event or activity that pertains to that particular set of photo's. Then you group all of those folders under a folder for that specific month. Finally, group all of the month folders into a Year folder. My aperture layout looks like this: