Jump in with digital. I did it years ago after some very successful time with my Nikon F2. Still have the F2 but have not even taken it out of the case for a loooooong time. As for digitalizing your old photos, you can get a pretty good flat bed scanner for cheap, scan them and have all of those old photos to send in emails, make slide shows......all kinds of stuff. Digital cameras are so easy to use, and unlike a film camera, you have instant results and if you don't like it, erase it and do it again. Nothing worse than taking that shot of a lifetime with a film camera only to find out a week later when you have the film developed, it didn't come out. Good luck.