My Vp44 is going bad. I was looking at Pensacola Diesel who offers a vp44 package deal that comes with a Air Dog 100 for $1300. Is that a good set up/deal? Also what do you think about Bosch 275's while I'm at it?

 

IMO the 275 is a waste of money.
The rest seems like a decent deal to me.
And, welcome to the club!