I was never that impressed with the previous gretsches myself, just didn't have the woodsy bark i was looking for.
There are still people that love the old pod 2.0 models, it's all opinion.
feature wise 1.9, doesn't have alot less, if you ended up staying there most of what you'd miss out on is the new workbench...
i think workbench is going to get alot more use now that it's left it's "word perfect" ancient GUI.
i bet you'll be able to address alot of your concerns and ultimately be swayed to 2.0 with some tweaking in workbench...
but just in case... i've reflashed in a couple of instances when i didn't think things were right...
and things got right.... so a reflash is ALWAYS worth a try IMO.
So far, I'm disappointed with V2.0. There were only 5 models/modes of the older firmware that I liked enough to use: Spank positions 2 & 4, Lester position 1, Jangle 2 (12 String electric) and the Coral Sitar. With V2, the Spanks have changed radically, I absolutely do not like new sounds and the Lester seems to have lost some of its "bite". I cannot hear a difference with Jangle 2 or the Sitar. The Tele sounds are an improvement over what was there before, but still not a contemporary Telecaster sound. The RBilly models still do not sound anything like a Gretsch (I own 4 Gretsches, I know what they are supposed to sound like). I already assumed that the acoustic models would be the same crappy models already released, and I was right. I can't use them for anything, anyway.
The WB is a big improvement, and the output level issue is at last controllable (one of my big beefs with the JTV removed). The WB UI is great, however their are bugs - for instance, have any of you tried to open the Preset Folder (in the "File" menu)? I get an error message on my MacBook (OSX Mountain Lion). Maybe the Windows version works.
I'm going to keep exploring the new HD models tonight ... maybe I missed something.