Ok I figured out the "view full screen" toolbar icon will make it windowed (Menu bar, toolbar and remote view all in one window). This was misleading to me because "view full screen" makes me think of Remote Desktop if you maximize it. View full screen in dameware simply to me could have been called detach toolbar from remote view.
Any way to make it default to keep everything attached?
Ok I found it after trial and error.
View > Local Global Options > uncheck Resize Window on Connect.
Again this language did not make it clear to me this was what needed to be checked off.
Not sure what triggers a resize, but with Smart Sizing you really don't need 1:1 pixel mapping. My main monitor is 1920x1200 and my secondary is 1280x1024.