Killdagger,
Actually it could be either or both. There are a number
of things that could be wrong, but starting with the radio,
try another antenna to see what happens. If the output is
good then I'd take a look at the antenna. There's nothing
'wrong' with using a dipole, they're good antennas (no matter
what they cost). If the 'match' between radio/feed line and
antenna is bad it usually will reduce the signal you transmit
but will very seldom reduce it as much as you say is happening.
Another thing you might consider is the polarity of the
dipole. Hung as an inverted 'V' it will be horizontally
polarized, which will further reduce your signal (if the guy's
antenna on the other end is vertical). That only happens at
fairly short distances, on long distances the polarity changes
after the fist 'skip'. After the first 'skip' you really don't
have any idea of what the polarization is...
'Doc