Agreed on the bromination not coming out right.  The finkelstein is so straightforward, and the amination, despite being a very involved procedure, is also pretty straightforward.  And there's the issue of my "bromosafrole" having a lower than expected density.

I'd very much like to try simply stirring safrole with 33% HBr in GAA, without any of the NaBr/H2SO4 possibly mucking things up.  With the way jon describes I see the possibility of H2SO4 causing issues (ether cleavage perhaps), and the potential for too low a concentration of HBr due to the low solubility of NaBr in acetic acid.

As for generating clean HBr -- haven't heard of the tetralin method but I don't doubt it works.  Problems I see is that obtaining Br2 in bulk quantities could be tedious, and that tetralin doesn't look particularly OTC.  But I didn't do much research on that, so I could be wrong.  I've tried 85% H3PO4 and NaBr if that's what you're referring to.  I heated and heated to the point of reflux and barely got any gas generation.  Not sure if I was just doing something wrong?

I'm taking a break at the moment to work on some other stuff but I really want to revisit this at some point.

why not use an easily procured test substrate until methods are refined and then break out the sass?

jon said star anise works, just toss the end product