I am sorry for not givena any answer. So I will take them step by step.
On the first question the 1H-phenalene has 12 pi electrons ( not obey the 4n+2 rule) therefore i am thinking that maybe it is not aromatic, although the molecule is formed by fusing 3 benzene rings.
On the second question if you think of -OTs the first though will be as a good leaving group, therefore a carbocation is formed. The synthesis should not work in this case.
Hope now it is ok