I get it, people are broke, and spending more on a piece of furniture than you did on your first car is tough to justify when Wal-Mart is just down the block. However just because you don’t want to spend a lot of cash doesn’t mean you can’t get quality furniture. You just have to look around, stay patient, and know a ot about what you are looking for. If you know something the seller doesn’t, you can get a great deal. If you are lucky, you’ll find that vintage Patek Phillipe in a good will display case for $20. (Metaphor, but I still check Good Will for it occasionally)
When you do the flea market and estate sale route, you want to avoid anything with a cushion. An dresser or a dining room table won’t have fabric and or padding fatigue. However if you pick up a love seat from the Nixon Administration, you will probably get a less-than-comfortable couch with a good amount of fading and wear. Dining room chairs are the exception, because reupholstering these are normally fairly simple and require little padding. I would avoid setting you heart on finding a sofa or a lounge, but instead try to limit your flea market endeavors to wood furniture if possible. This way, if you wind up finding a quality chaise or sofa, you will be pleasantly surprised.
The biggest tip is to know your brands. Don’t assume they know nothing about what they are selling, but make sure you are going into an environment where you know more. Look for companies like Drexel, Century, Ethan Allen, and Durham are great to look for. These are quality built pieces that are made to survive numerous decades. If you were to buy these new, it would cost you about the gently used, mid decade sedan. I picked up a 7 foot Drexel solid oak dresser and mirror for $250. The retail on this, brand new, would have been around $6,000.
Be sure you haggle as well. People at a estates sale don’t have shareholders to answer to and paid rock bottom dollar for their merchandise. It should be fairly easy to take them down 10-20% depending on how much time is left at the estate sale. If it is a Friday-Sunday sale, like many are, if you believe the piece you want will still be there, you should wait. It is a risk, but it could save you some money.