The trouble with Song of the South is that it ignores the issues of the Jim Crow south, and presents the ex-slaves(?) around grandpa’s plantation as happy-go-lucky, well fed, decently dressed, respectful servants and workers who knew their place and were well-treated by their paternalistic employer. It made a too-good representation of the situation, and potrayed the situation as white people probably wanted to believe it was. The bits I’ve seen - I fast-forwarded through some of it - would be more racist in their “why are you complaining?” sort of presentation of the black situation. There’s no scenes, for example, where Uncle Remus or the others, or the black playmates, are told “you can’t come in here” or anything like that.
From the clothing and horse-and-carriage it does appear to be set at least 1900 or earlier.
Of course, it’s a reflection of the time in which it was made. There are plenty worse, actually offensive depictions of black people in Hollywood in that era. But to Disney’s credit, they;ve recognized the problem and restricted its availability for quite a while. (Much as Peter Pan, with its depiction of North American natives, is “iffy” today… especially with a song like Why is the Red Man Red? )
The past is a foreign country. They do things differently there.
-L.P. Hartley