The file you're trying to upload seems to be the SqLite database file, the correct file to upload is forgottenserver.sql.
have you tried to re-download the server?
wingui has a GUI - Graphical User Interface while winconsole is just a cmd window with the information.
The WINGUI has some extra features you can control outside the server, like reload actions, talk, move etc. and broadcast and so on.
Well, ya, if you've got the server hosted on your own computer, else it doesn't matter.