The spirit of Oldhammer is difficult to identify but I think its a case of an elephant.....you know one when you see one
If a figure is the latest fine crap resin casting painted to current competition standards and style, I suspect it wouldn't get the spirit of Oldhammer tick. We would probably be looking for classic models painted sympathetically or even modern production painted as if they belong on a tabletop in 1989 rather than 2013?
Personally I would get a panel of judges (say 3) and ask them to rate each entry using a set of flexible guidelines, for example:
1) Quality of paintwork, does it show good technique, freehand work etc.
2) Choice of model...... does it embody Oldhammer or is it 'out of place' in the competition?
3) Quality and style of basing.
4) Any extra factors for which credit should be given such as conversion work or anything else not covered above.
Those are off the top of my head but something similar would provide a structure and framework by which to consider each entry.
Oh......... I would also restrict entries to physical attendees which I am sure will upset some board members, but there is nothing more of a let-down than a winner who isn't there to receive their trophy.
Other points to consider are when the judging takes place and when the prizes are to be awarded. I was personally only present on the Saturday and I don't think I was alone in that. As a two day event it makes sense to award the trophy at the end of the event on Sunday afternoon. The judging could however be done on the Saturday so that models didn't have to stay there for the whole two days. Thoughts anyone?