This is the way I see it. Drakov's curse is multifaceted. He can't win a long term war (any victories he has are ultimately phyrric). He also cannot get proper respect from those he wants it from (Strahd, Azalin, and the other 'strong' rulers) , or he gets obsequious praise from women and fops (the Boritsis, D'Honiaire), which humiliates him in its disingenuousness.
So what does Drakov do? His country gets criticized, so he tries to deal with the problem as he sees it. No opera like in Port-a-Lucine and mocked for the lack of high culture? Drakov has his subordinates make grand opera in Silbervas, but he gets no credit for it. Forward thinkers at the University of Il-Aluk have a Department of Arcane Studies? Vlad has the Falkovnian Ministry of Arcane founded at great expense, which technically makes him one of the most open minded and progressive rulers (technically only because some sinister stuff is happening at the ministry). Vlad still doesn't get respect. Poor roads? Vlad builds the best, widest road system in the domains, and is accused of building the roads for rapid troop movements.
Not only is Drakov unable to win permanent victories, his various actions are doomed to be seen in the worst possible light. If there are various ways to interpret Dravok's words and actions, the worst interpretation is always taken (only outside of Falkovnia). This is why Drakov has the reputation of a buffoon, a thug, an incompetent, and an efficient killer all at the same time.
Lastly, as far as I know Falkovnia does not have an official state church. This seems one of the bases that Drakov would be unlikely to overlook, especially since he came from Thenol in Krynn, which was more or less a theocracy under the clerics of Hith (Hiddukel). Drakov surely has a state church.
I am not down with the canon, incompetent buffoon that is Vlad Drakov. Drakov has skin in the game. As a mercenary commander on Krynn, failure means death. That means that the incompetent are filtered out. Drakov isn't a no skin in the game armchair strategist like Bill Kristol who has been wrong about everything for the last two decades and never faced any negative consequences. See Nicholas Taleb's 'Skin in the Game'.
If Vlad is a big loser, then his curse isn't really a curse. There wouldn't even need to be a curse of always losing wars if he was going to lose them anyway. It would be redundant.
Vlad Drakov's 'curse' is the lamest in the entire Ravenloft setting. If he is such an incompetent buffoon, there is no need to curse him with his own state and have him fight battles that he loses due to his own shortcomings. A real curse for Vlad would be losing despite doing everything right - or everything right with the information available to him.I buy very little of Drakov's shortcomings. Supposedly he is so set in his ways that he refuses to adopt new technologies and deploy new tactics. He keep doing this despite continual failure. Is Vlad Drakov simply autistic and not evil? If this is his problem, it would seem so.
His curse is to lose his wars. If he's responsible for losing the wars anyway then it is hardly a curse, is it? It lacks pathos. Turn this on its head. Instead of being an incompetent buffoon, Vlad Drakov is actually a brilliant tactician that does everything right. Despite mastery in directing the field of battle he always loses the wars at the end, and the best that Drakov manage is a stalemate.
Instead of Vlad being an incompetent, Vlad should be very competent but loses the wars anyway. That's what a real curse looks like.