While it is probable/possible that a lot of the problems that people run into is the "burnt" on OOTB edges (although some may think this to be an urban myth, I've had it happen on pretty much all of my knives: the edge doesn't stabilize and degrade in sharpness consistently until one has sharpened enough steel away to get the the "fresh" steel underneath) I'm fairly certain that I've eaten through enough steel with my amateurish sharpening efforts from years back on diamonds. It's probably 2 mm shorter than when I first got it.
Now I'll typically flatten the bevel a bit (maybe one minute or two) on a 1k Shapton, move to the a 2k Shapton, then to a 5k Shapton. In the past month or so I've become enamored with the edge that I get from going directly from the 2k Shapton to edge trailing strokes on a Spyderco ultrafine benchstone. I'll maintain that edge with a 1 micron diamond paste loaded strop or a strop with 0.5 micron diamond spray until it starts getting to be a few too many strokes on the strop for my liking to bring the edge back.
The edge stays sharp for a good amount of time. I'll typically not need to strop the knife for a week or so (I'd use it 2 - 5 times a day), until I feel like I've lost the scary sharp edge and bring it back with a few passes on the strop. The edge that doesn't chip out stays sharp and in truth it shouldn't bother me since it doesn't really have much of an effect for the majority of the stuff I'm cutting. Again, it's just a sprinkling of chips on the edge.
You might just have bad knives (it happens), or they just don't work for your uses (that also happens).
when i sharpen co workers shuns i finish with green brick and strop. i liked that edge better than rika 5k or other higher grit stones i use
I've had 3 shun chef knives. One I never used and the others 8" classic and 'western' chipped to hell OOTB and are missing tips. One fell to the floor and the other got tapped on the table as I was raising it to put on my bag. The classic has been sharpened on stones a few times and is now OK. The western one sharpened once on stones and has 2 decent chips near the heel. I found using a steel destroyed them. I hated seeing chips cause I never knew where they went. OH well I don't use them anymore and keep one in my bag if I think I'll need a knife but there's a chance to be knocked around a lot. It's funny cause it's still one of the sharpest in the kitchen I'm in now but they wonder why there's accordion cuts :)
Shun - curing iron deficiency since 2003
I have a Shun that used to be my prized possession, now it is my beater knife.