I've done the retail flip thing a few times over the years. My best deal ever was buying a $12 bohemian czechoslovakian, golden, hand painted goblet at an antique mall in Florida and then resold it on eBay for over $80.

I did vintage and antique pieces. I hated reselling clothing for the reasons you mentioned. I had to take a million and one photos of single piece of clothing from every angle imaginable and would still get questions. To me it just wasn't worth it.