My own suggestion is to try the antenna first (a high gain like the CM4228) before trying the pre-amp. The pre-amp can always be added. There is always the possibility of too great a signal - and causing overload. I'm in Thornhill, not far from Richmond Hill. But then it also depends where in Richmond Hill -- high or low spot. It' a case of the more the better, up to a point.
The CM4228 provides a reasonable pattern, with about 12dB UHF gain. A pre-amp, like the 7775, will add another 23 dB. Remember, there is loss in the cable, loss in the connectors (about 2-3 dB total).
If you have diplexors or splitters, another 3-5 dB loss.
Just my 2 cents worth.