The kids grumbled a lot about the destination–too much like a school field trip, but once our tour got started they were totally engaged. The museum, simply put, is a tenement apartment building, but it's changed little since the 1860's when it was built. We learned that four families lived in identical apartments on each floor of this five story building sharing four outhouses and one water pump out back. The intricate scroll work and moldings in the building were unexpected, but the dark, musty quality of the spaces was what you might imagine. We heard a recording of a woman who lived there during the Depression. Our tour-guide told us a dickensian story about one family living there during the 1870's. A fascinating account of the time and all documented. 
I've got to go back to the area sans kids to explore more fully, but we did manage to pop into one store worth a look-see, a haberdashery called Freemans Sporting Club. There is a classic barber shop in the back of the store right out of the movie, The Sting. Suits are made to measure using vintage fabrics, the workmanship, impeccable.
The Blue Moon Hotel at 100 Orchard looks interesting and has reasonable rates. Imagine staying there, strolling to the corner cafe for a latte and chocolate croissant, visiting the Tenement Museum, popping into any one of the hip looking stores and galleries neighboring to the museum, and then rounding out the day with dim sum in Chinatown. Without the hotel stay, that's just about what we did. A great day in the Orchard.