Seen them all, seen some people just one or combos of these, but what are the advantages to each? I suppose the disc would be difficult on a windy day. Tri spokes look really cool, but are the faster than a deep rim like the 808's? Are the deep rims best for all conditions?
Any light on this subject would be much appreciated.

Wind effect depends on your weight. Lighter riders have more difficulty. I think HED 3's and 808 are the same. Difference would be the 3's would give a changing effect to strong side winds depending on the angle of the arm to the wind. 808's will be consistent. If winds are really high in your area, look at the HED alps, not much lost in aero advantage and much better in the winds. If you can't afford two wheels at this time, put on the front first and then the rear. Oh, I don't know of anyone that rides with disc in front.

A cheap way to get a rear disc is to get a CH Aero wheel cover from wheelbuilder.com. Runs $60-90, depending on the wheel you've got. I have an American Classic Shimano rear with a Powertap SL hub that I train on. 5 minutes to put the wheel cover on and I have a disc to race on. The wheel wind tunnel results over on biketechreview.com have this setup right up there with the `real' discs (Zipp, Renn, etc.) and faster than all the non-disc wheels.