It would be a good idea to do some testing on the beta server before using the GWtoolset in production, it's a lot of work to make changes to large numbers of files on Commons. These type of mistakes will then be filtered out by the time you do a batch upload. Here is a write-up of my own workflow.
As for filenames, each name must be unique. So try and create a unique name by using e.g. the title field, identifier field and date as a combination. 

Good luck,
Jesse

2015-07-27 16:14 GMT+02:00 Jason J. Evans <jason.evans@llgc.org.uk>:
Sorry to keep asking so many questions, but i have noticed with our upload of Welsh landscapes that several different images often have the same file name. Each upload is just replacing the previous file by that name. Is there some way to give each 'version' of the file its own page on commons or would i have to manually identify each one and re-upload with new file names?

here is an example: https://commons.wikimedia.org/wiki/File:Brecon.jpeg


Thanks

Jason





On Monday, July 27, 2015 11:49 BST, "Hans Muller" <j.m.muller@hccnet.nl> wrote:

> Now some uploads run fast in the foreground and of course win over a

> background GWTs-job (~100s x slower). Perhaps we should share the room
> more equally, slow uploads can endanger projects, less to show to donors.
>
> Regards, hans muller
>
> Op Vr, 24 juli, 2015 5:02 pm schreef Brian Wolff:
> > On 7/24/15, Jason J. Evans <jason.evans@llgc.org.uk> wrote:
> >
> >> Thanks Brian
> >>
> >>
> >> Yes more have now uploaded, but it will take days at the current speed.
> >> Does
> >> the process time-out at all or will it keep going as long as our servers
> >> are running?
> >
> > It should keep going forever.
> >
> >>
> >> Also, do you have any suggestions as to why some images are timing out?
> >>
> >>
> >> Thanks for your help.
> >>
> >>
> >> Jason
> >>
> >
> > I don't really know. The rate limiting mechanism for gwtoolset isn't
> > the most smooth. Perhaps its trys to load too many at one time (overloading
> > things for that instant), and then does nothing for like 20 minutes.
> >
> >
> > --bawolff
> >
> >
> > _______________________________________________
> > Glamtools mailing list
> > Glamtools@lists.wikimedia.org
> > https://lists.wikimedia.org/mailman/listinfo/glamtools
> >
> >
>
>
>
> _______________________________________________
> Glamtools mailing list
> Glamtools@lists.wikimedia.org
> https://lists.wikimedia.org/mailman/listinfo/glamtools

--
Jason Evans
Wicipediwr Preswyl / Wikipedian in Residence
Llyfrgell Genedlaethol Cymru / National Library of Wales
jason.evans@llgc.org.uk
Ffon/Tel: +44 (0)1970 632405


_______________________________________________
Glamtools mailing list
Glamtools@lists.wikimedia.org
https://lists.wikimedia.org/mailman/listinfo/glamtools



--

Met vriendelijke groet,

Jesse de Vos
Researcher Interactive and New Media

T 035 - 677 39 37
Aanwezig: ma t/m do

Nederlands Instituut voor Beeld en Geluid
Media Parkboulevard 1, 1217 WE  Hilversum | Postbus 1060, 1200 BB  Hilversum | beeldengeluid.nl