I bought a Thomasville Winfrey chair for $40 used last year, and have been holding off on having it reupholstered because of the cost. I've tried slipcovers with arm padding, but everything just looks weird on it. The current fabric is in terrible shape, but the structure is like new, and the wood is in great shape.
Since you only paid $40 for it, the $350 is certainly a reasonable alternative to new. In most cases. reupholstering is much more expensive than buying new but if you know that the chair is $900-$1200 new, this is a bargain.
If the structure is in good shape and a new chair would be at least $900, then yes, $350 to reupholster the chair is worth it. Thomasville furniture is good quality and as long as you get a good upholsterer to do the work, it should last a long time.
