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Unfortunately you just have to plan ahead for all options. If you need it to be sunny outside then plan for that, but take some umbrellas and think, does the script Need it to be sunny or does it not matter? That said, it is preferable to get what you want, but you really just have to cross your fingers on this one. Allow a shooting bracket, a series of days where you are available to shoot so if one gets rained out then you can use one of the spares. If it's cloudy or the light is a different look from what you want, you can always post-prod it easily. Hope this helps :)

You could do this with good ol' clever shots if you're stuck for a solution. Make every character wear the same shoes and pants, something really generic, or at least the same colour. Then shoot your talent, the multiple people along a street or wall or wherever you are using a long track dolly so you can basically recreate the shots each time. Then just get footage of the feet, legs and the dog walking. Whenever you need to switch people, just cut to that footage (or similar non-upper-body showing footage) and then cut back. If the dog is the same and they're in the same location then the continuity will be restored. You could add to the continuity by adding some posters or peeling paint or something noticeable behind them and when you switch between the shots of different talent cut to the same basic point in time so that the recognisable marks carry along as if in a normal dollying shot. Hope this helps!

Whatever you do don't use digital rain in post. It works fine if you've got a completely post shot or if you're compositing something else out a window, but not for external shots. I'd say spray a hose into the air from the sides and move it around a bit. If you need different angles of spray, take several sections of the shots and mask them together so it looks uniform. Hope this helps and good luck :D