I've pondered making wine generate a file full of "add-symbol-file" commands or something that could be executed by gdb, but I don't know how to do that cleanly... preferably hacks for loading symbols should be transparent to the developer, and new symbols loaded automatically after new dlls are loaded. Hmm...
is the configuration variable 'auto-solib-add' set to 0 or 1 after switching to the remote mode ? if this doens't help, you could also try to set stop-on-solib-events to 1 it won't directly help for loading symbol, but it's the right place for hooking shared lib symbol loading
HTH
A+