Just some random thoughts and my observations based on watching places operate, and my prior experience running an auto service shop. I have also thought about this path for "retirement".
I am a former ASE certified Master Tech, have an Auto Tech Associates degree, have a Bachelor and Masters in Mechanical Engineering, and 19 years experience in a variety of development, design, manufacturing, and project management roles on top of my 8 years as an auto mechanic. I was heavily involved in round track and drag racing when I was younger and even worked at MSD (Autotronics Corp - El Paso, TX) for a short period in the 80's when I was a student.
This business is hard to model in the traditional sense, the body, paint and fabrication work still require some level of craftsman / artist type work which is difficult to estimate. The variation in the work is also hard to get a handle on, most vehicles need to be taken down to bare metal before you have a good idea of the scope of work. With sufficient experience base I think one could get reasonably good at estimating. I think the problem also lies in the fact that if you have to do a large amount of sheet metal replacement, bodywork, and paint then your time and materials will quickly outpace the value of the vehicle in most cases.
I think some of the really big operations have good project managers / shop leads. The problem is that in order to be efficient, you would have to have some scale and have a group of workers with a variety of skills and some flexibility. The issue this creates is that you need a workload that can keep this machine fed. The few shops that seem to be able to pull this off and do well have a customer base with deep pockets and run a large number of big projects with long timelines. Then you can fill with smaller projects and schedule work around the bigger ones. That kind of customer base only seems to be available to a few shops with reputations of building top level show winning cars. Kindig, Foose, Strope, Trepanier... and I think the common denominator on these guys is that they are artists first.
Other shops, like DSE, have a core business that involves selling a product. The builds in their shop seem like partly R&D for their products.
Finding and keeping good tradesmen is a difficult task. Having a good recruiting practice and good people management skills would be key, it would also be helpful in dealing with customers. At some level you may also have to make a call on what you can do in house and what to farm out. For example, I know a local shop that does custom upholstery, headliners, and convertible tops that would be hard to beat.
And you forgot about Problem #5: A lot of customers have cash flow issues... real or perceived. I have seen a lot of projects stall because the customer stopped paying.
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