Re 1., gravity has infinite range, so the effect of gravitational time dilation will just grow weaker, but theoretically not go away entirely.
In the idealized case of a single source of gravity, the time dilation factor is given by
$$
\frac t{t_0} = \sqrt{\frac{1-\frac{r_s}{r}}{1-\frac{r_s}{r_0}}}
$$
where the Schwarzschild radius $r_s$ represents the mass of the source, $r_0$ the position of a clock close to the source and $r$ the position of an observer that sees the clock as having slowed down by this factor.
Re 2., transmission times would also increase by the factor above. If you want two-way communication, you also have to take into account the travel time of the signal. While I did the calculation, I'm not sure how interesting that expression would be for you (it's less nice than the term above).
Re 3., depends on your mode of transmission: I imagine you'd have to properly restore any digital signal before it could even be decoded, but once that's done, playback would happen without any slowdown. On the other hand, ignorant person that I am (ie without having looked at how radio actually works), I'd expect a direct playback of an analog radio signal would indeed be slowed by the factor above as well (and possibly otherwise distorted, in particular in case of frequency modulation). Also note that the carrier wave would be shifted towards longer wavelengths.