Thats my friend Cameron Jurow http://www.camtechcustom.com/ with that display of custom baggers. The attention to detail in his bikes are unbelieveable. He has a few builds going on now that are going to really push to custom bagger envelope.
I have never rode a raked bagger with a 23", 26" or 30" wheel but he said its just like getting used to riding with a 21" for the first time. From what I'm told, when they rake and stretch the neck, add the raked tripple trees it handles just fine. Its not like putting a 23" on a stock rake bagger with stock triple trees. I know for a fact that he can still horse around on them and ride the wheels off them, wheelies, burnouts etc.
I like the big wheels but it costs a lot of $$$ to get done to your bike. I also agree, its just the next big fad in the industry after the chopper craze. Looks like the 21" on my SERK will have to do the job for now.