Awesome. I think if I'm going to have any trouble with overlap, it's going to be with Wavelab. Steinberg uses the eLicenser dongle thing. I guess I don't know if there is going to be any issues, but I'm just really unfamiliar with the whole eLincenser thing.

If you can, pull the harddrive from your old DAW and install it in your new one.  You will be able to get all your projects (just point Sonar to the drive and directory).

The e-lincener should be plug and play - ie, it will only let the software run when it is plugged in.  Makes it easy to switch machines - install the software and switch usb slots.
 
If you can switch your project hard drive that is good, too.  You can re-assign the lettering on your new computer if necessary and simply point your projects to that drive with all the sound files.
 
Don't worry about loading in old versions of SONAR -you can just load in whatever effects you want from that version by doing  a custom install.
 
DAW, stereo editor (wavelab or Sound forge), video (Vegas for me), then on to the synths, finally effects.  That is how I load in programs.
 
@

Actually, the most important tip is to BREATH!!!!!!!!!!!

The best process for using different DAW's is a filled Master Card.

The one thing I would recommend:
If the new system you buy is a commercial system with a pre-installed system, I would advise borrowing somebody's purchased CD and do a re-install to get rid of all the garbage that comes with pre-installs. If you install the same version system (e.g. Windows 7 Professional 64-bit) you can re-use the registration code that comes with your system (generally on a sticker attached to the system, but you can also read it from the <Control Panel>-<System> page). 
 
Most people neglect this, but in the long run it is a HUGE advantage. 
 
Also, locate all of your plug-ins and loops and copy them over directly to directories on your second non-system disc drive (you ARE planning to have 2 drives??). Then you just have to install the core software and only the new add-ins. the first scan will find everything, including all the things that you bought outside of Cakewalk.

If you use DimPro, SampleTank or any other softsynth that relies on multisamples, there is no need to install the multisamples from scratch onto the new PC.  Just copy all the multisamples over with the folder structure intact.
 

Good info. I have all of my project files on a separate drive and will be moving that to the new rig. The DAW is a custom DAW from ADK so other than their backup software, there shouldn't be any junk on it.