Re: boba vs. dengar
while the fetts are techinacally sound fighters, we know they arent much when they enter the fray. for examples of this see the sarlacc or the arena. dengar is like that burly ogre- you definitely want this guy on ur side in a bar fight, yep he's bloated and probably lost a step but im thinking he can take a punch. so this seems like it would hinge on too many variables.
fett always seemed like the smartest guy in the room, not the toughest.
They're ok when they enter the fray.
I think that the battle may last one second, at the most. In Tales of the Bounty Hunters, Dengar, with his emotions still removed, attacked the half-dead Fett, and Boba bested him in maybe four seconds. Boba had no armor or weapons, other than a blaster that I think he took from Dengar in mid-battle.
For once, I agree with you