I've only ever had one so can't help you there.
I polished off a bottle of E&J Brandy with cranberry juice the night of my Gramp's wake. Apparently during that episode, I chunked all over the table at Chili's, got kicked out, handed my wallet plus ATM pin over to my cousin so he could get more party favors, chunked in my bud's new Explorer - twice, and called dinosaurs (that's what he called hurling) all night long. Bonus was his hot sister was holding my hair back so it didn't get in the toilet the whole time, and I'm pretty sure I touched her boobies. I don't remember any of this, only time I've ever blacked out and lost time like that. I had to clean his Explorer the next day. I just stay away from Brandy now. Ironically, tequila has almost no ill effects for me.
So I got no experience with hangovers beyond that one.