What is the hardware you are running this on? I have been using a mix of Disk Images & WDE for several years.
First PGP with Windows XP (WDE on 7400 RPM), and then after I got a mac both Filevault (not WDE on 7400 RPM) and FileVault 2 (WDE on 740 RPM and SSD)
My hardware is capable enough that I virtualise rather than dual boot. 10.7-9 with VMWare fusion running XP/Vista (ugh) / Win 7 and now Win 8.1 and even at one stage Ubuntu over the years.
Doing it this way means I can flick between multiple systems without a reboot, they use saved states and I can rely on a single platforms built in WDE to reduce the complexity.
however, whichever path you choose, you need to decide why your encrypting, and make sure you have backups.
If your drive fails, your not going to be able to recover data easily, like you can with non-encrypted data.
The devices I encrypt, are the ones that are portable. I am not worried about the safety of the desktop I have, but the laptops I carry around to work, that have confidential data etc I do encrypt.
I have a mix of backup routines, every OS upgrade I do full clone of my HD, excluding the virtual machines and data stored elsewhere on my NAS. I have two encrypted time machine backups, one on a 2.5" HDR and one on a time capsule. I also use crash plan to backup pure data directories. I backup media such as music/videos etc manually.
Photos are captured in my time machine backups, and if have an aperture vault, as well as exported projects and an export of any adjusted photos in JPG that are accessible via the NAS.
email encryption is just the default provided by the host, but I don't setup any non SSL if I have any choice. I have demod how easy it is to access this to people before. if I need to do net banking on external networks, I establish a VPN home and use that to connect from a trusted network.