Kyle,
I cannot really try, because I do not have your data, but maybe when you write your code in a more "step by step" manner, I cannot see why things should not work, e.g.:
ri = ImageResize[#, {40, 40}] &@*ExampleData /@ {{"TestImage", "Girl"}, {"TestImage",
"Girl2"}, {"TestImage", "Girl3"}, {"TestImage",
"Lena"}, {"TestImage", "Tiffany"}, {"TestImage", "Mandrill"}};
data = Table[{DateObject@RandomInteger[{0, UnixTime[]}], RandomInteger[100]}, {r, 6}, {c, 10}];
dlpl = DateListPlot /@ data;
TabView[MapThread[Rule, {ri, dlpl}]]

BTW: Nice idea to use images as tab labels! Regards -- Henrik