We've had our dining room set that we purchased for $100 at an auction for 11 years. It is scratched up but it could be sanded and painted. dh doesn't think there is anything wrong with it. It looks very outdated to me. I also have a hutch type thing I'm using for a computer desk that I want to paint to match the table and chairs, since its in the dining room.
BEFORE
The tablecloth and place mats look tacky. I don't know what I was thinking... anyway.. this is my before photo.
PROPOSED











and sanding but then I'd just paint them black. I'd also move the table from the wall, put the 4th chair there and put the 5th in the corner like suggested.