(1) HOA rules regarding antennas, are generally silly and unenforceable.
http://www.fcc.gov/guides/over-air-r...n-devices-rule
HOAs are perfectly aware of this and are just hoping that you aren't.
Signals do not like to travel through building materials and any borderline signals will almost certainly be blocked.
Aiming through the roof from outside, will be even worse.
(2) Yes, multiple antennas or a rotor, depending on whether there will be multiple TVs, or if you're recording.
(3) That depends on the length of cable run, and/ or number of TVs.
(4) P.E.is a great place to do business with, but for antennas, you want to deal w/ a company that specializes in antennas.