Eh, I still wouldn't go for the jugular of a side that looked empty and had a treasury that size.
1. The decrypted troops dusting is a bit of wishful speculation.
2. Jillian made a hit and run attack on poorly defended cities in attacks of opportunity. It was very clearly stated that the breakneck speed of GK's conquests had left them tragically overextended.
3. Don also knows that any infantry can be promoted to knights so Stanley automatically has more knight class units than TV and FAQ combined even if all the decrypted dust. 2 mil is a lot in Erf.
4. How does Don know Stanley doesn't have any gobs? I'm fairly certain that whole thing is very hush-hush. Even if they were told, assuming no new natural allies should be assumption enough to check yourself and think "gee, maybe I am being a little optimistic." Again, I'm strictly arguing from a 2 mil bank account imperfect information enemy.
5. Assuming GK can hire casters (I don't. Bad relations now) What makes you think a medium size air force and one level 10 warlord can defeat 500,000 schmuckers worth of MK goodness, let alone a million if Stanley wants to get extravagant?
Because of her track record. Don trusting or not trusting people based on their birth status is idiotic.Jillian would be another royal side. Why would Don King not expect her to be a good ally?
I don't think Jillian could hold on to many cities she captured, though. TV might help, but it sounds like they don't have people to spare. I think she would raze them and turn anyone the managed to capture.
I don't think she could hold them either. I don't think TV can afford to help either. I think that is what she would do as well.
Which leads us back to: Don is super proud that his money sink is going to go make some easy money off of a dangerous, incredibly wealthy side. TV gets nothing except a chance to convince GK to end them.