How much work can you do yourself, and how much would have to be done at a shop?

Here is where I am at; I enjoy working on the cars as a hobby, and I know that I will be doing more than one car (I have alread done a dozen partial restorations), so I have no issues investing in some of the more expensive tools like a rotessory, compressor, welder, air tools, etc. Eventially I will get around to doind a full restoration on the Convertible. I was going to completly re-do the Coronet 500 too, but the wife needs a driver, so I have been considering just a quick re-paint even though I know a few years down the road I will want to completly re-do it again....

I guess alot depends on how nice you really want the car to be? I believe it is true that it is less expensive to do the car once than twice, but the reality is it could cost $20,000+, but when it is done it will be nearly new, and most new econo-boxes are around $20K, so which would you want to drive?