Arylic vs benzylic carbocation

For the first addition reaction, when the curly arrow goes from the pi bond to the H atom, I wonder where to place the H atom as both sides of the alkene have 1H attached. I am not sure whether an arylic or benzylic carbocation is more stable.

For the second addition reaction, there should be 2 products as the Br can attack from both top and bottom (stereoselectivity), resulting in enantiomers, right? (But when I've drawn them, I've got the R,S product only...)

Brumer