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there are alternatives to std::stringstream, e.g:

String path = format("C:/Users/Sam/Desktop/HumanCount/Training Images/Content/positive/%04d.JPG", i);

or avoid the whole number parsing:

vector<String> fn;
glob("C:/Users/Sam/Desktop/HumanCount/Training Images/Content/positive/*.JPG", fn);
for (auto f:fn) 
    Mat img = imread(f,IMREAD_GRAYSCALE);

but the main problem in your code is a silly typo:

os << " C:/Users/ .....
       ^ there should be no space here, right ?