No. In the presence of peroxides, the reaction is anti-Markovnikov selective. See: https://www.masterorganicchemistry.com/2013/04/12/addition-hbr-alkenes-roor-peroxides-free-radical/

Protonation will occur so as to give the most stable carbocation intermediate. In that case it’s not very clear which one. But what will happen after protonation is that there will be cyclization to give a new ring, followed by addition of halide ion.

A small amount of the “anti-Markovnikov” product will always form. A ballpark estimate is 80 / 20 ratio of markovnikov to anti-markovnikov but it can vary considerably.

No, it is irrelevant to steric hindrance.