I have had the same setup been tested by two different pen testers, so yes, I would not mind that bet.

If you break the law however, which is what happens if a pen test a system without permission, then it doesn't really matter if you hack or use rubber hose tactics. Breaking the law is breaking the law. The police don't look kindly to bets under those situations.

I will also say the same thing I wrote to those two pen testers that tested our system. If you find any vulnerability I will happy help write the CVE report. What I did not tell them but will mention here is that I also happy take part in getting those bug hunting reward money that zero days exploits usually rewards. If you have for example a working exploit against current stable release of latest SSH then I am sure we can turn that in somewhere for a pretty good amount of money.