Situations like this...
You make several bids for players equal to your available funds... you then make upgrades to your club facilities before the bidding time has passed and use all of your money... you then win all of your bids you made earlier!
... Will make you go into serious dept at your club!! Experience talking
I was in negative for just less than a week and had no penalty... BUT i had already compensated with gate recipts and player sales before going into dept... otherwise i would have been in dept for a LOT longer
So in answer to your questions... you get into negative G by being... stupid with your money... and you can get away with... at least for... just under a week
The manual refers to actual club G holdings and not the finance balance sheet
Hope this helps