You're making the mistake of lumping every year since we moved in the same pot.
There was a very distinct period where we had no money, and then there was a much shorter period where we had some money and the potential to loan more if we wanted.
They decided not to and let Wenger drag them through (willingly) to this point now, where we have significant funds to spend on the playing side.
It was a mistake in some ways and a big gamble, but they pulled it off.