It only seems to have become a problem recently, after the debt started getting repaid and the Highbury development resolved itself, before that it was obvious that they were in it together imo.
I think he does tend to have more faith in players than other managers, some repay it like Song/RvP/Wilshere/Szczesny but some don't, like Bendtner and Denilson, it can be a flaw as well as a strength but it's served us pretty well so far (last 2 seasons aside).