I have been experimenting with using various file synchronising systems to "automate" my flow of photos (see also my ABC of photo flow post). At the moment I don't have a perfect set of procedures developed yet but I certainly have simplified my life a lot.
The basic principle is to have a set of simple to customise processes that will regularly check for new files and the also copy (or move them) to another location (or multiple locations) all transparently in background. There are lots of software packages that tackle this but after some experimenting I have chosen to go with Synkron, which is a public open source project and also available as a Portable App (so I can also have it on my USB Darkroom). However if you are new to the ways of file synchronization I might suggest you start with the elegant freeFileSync utility which has a simple drag and drop interface and separate compare and synchronization buttons to do the work. It can created batch processes for you but once you get the hang of filters and the difference between mirroring, two way synch and moves you will probably be ready to set up your own customized synchronisation task in Synkron.
I already have a task that backs up any recent photos loaded onto a photolibrary on an external backpack drive, I carry this around with me and thus backup photos there from any computer I'm using. I also have another task that synchs this library with a master photo archive, after I have run that I run another task that moves any movies out of the photo libraries to a shared video library location.
I have also set up some named filters (the example is one that I can use to move or copy just movie files). The real gem in the tools is Multisync, that lets you collect the files from several location (the computer doing the synch must be able to see all the folders involved) and can use Variables to tame the complexity of your Lan File structures. I am slowly prototyping the types of photo transfers I need and then as I find the right approach I customise and schedule a new task.
Warning :: Lightroom users take care
There is a massive word of caution here. If you are using lightroom, be warned it doesn't play well with file synching. Instead it wants to always be in charge of your files. The issue is the central but not shareable catalogue. This catalogue is where lightroom stores image previews and details of the post processing you have undertaken. If you synch the actual file directory you will only copy the original files and not be copying the editing carried out on the file. Picasa on the other hand stores this information in a file called picasa.ini which lives in the same directory as the original photo and is handled as part of the normal synch operations. lightroom is in reality a single computer single user system, and whilst you can store your originals on an external drive you must have a single catalogue that links to those photos. You can get around this limit by exporting catalogues and reimporting them, using DNG files to save you edits or using individual sidecar files (.xmp ) and I am still experimenting with all three alternatives but it still seems very messy me. I just have to live with the recognition that if I use lightroom on my laptop I have to make a special effort to “manually” make sure that any edits, tagging etc get into the master photo library. Perhaps this hassle is why I still prefer to shot both RAW and JPEG and use Picasa to load the photos and do the initial organization, ranking, and metadata tagging using the jpeg and RAW pair of files. Which is a pity because then a lot of the organizational power of lightroom goes unused.