Matt, as Andrew indicated above, if a connection came completely apart there would be a noticeable difference in sound quality; otherwise there's no good reason for concern about multiple connections.
Any of the gauges typically used for speaker wiring are more than sufficient for any of the power levels which are used in home audio. Items such as hair dryers and hot plates are significantly more demanding.
Among the online sources for no-nonsense info on speaker wiring needs,
this one by a respected veteran in the industry is probably the one most cited and valuable.
