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It is much easier to find and manage a qualified design/sales person than a project manager when jobs are high quality and of a complex nature.
I think that Bill's jobs fit this category. The jobs are built a certain way and the help is managed a certain way. When you replace yourself with a project manager there are lots of things that you take for granted that are very difficult for that person to overcome. The first is that you answer to yourself and yourself only when you make a decision. This person has to weigh everything against his perception of what he thinks you want him to do. That is a lot harder than it sounds and causes a certain amount of second guessing. From your perspective it seems that there is only one clear response that is the right one.
The project manager also has to come in to a new job situation where the existing crew is much more familiar with where they are, how you do things, and they view the project manager as someone that bypassed them without any right to the job. That person has to balance being in control and not fostering resentment and bitterness from the crew. It is not easy.
No matter who you get, the results will not be the same as yours and it breaks the continuity of your work. That is more true if you have to replace people at this position.
As for the designer/sales person, this is much easier because you can review his/her work before it gets out. Pricing jobs out can be made very quantifiable with little guess work. You can influence the design in style, materials, and everything else while using very little of your time.
When you have an outstanding reputation and portfolio, your biggest challenge is the built work rather than the design and sales as long as it is consistant with what you already do. The built work sells your jobs as long as the design/sales person knows what you are all about, knows what he is talking about, is confident, and exudes that confidence in your clients.
The hardest part of this level of landscaping is managing the construction and executing the job in the form of a built landscape.
I do design work for an outstanding design/build contractor. Rarely, but sometimes, the client will have someone else build one of our plans. Every design is paid for whether it is built by us or someone else, that is not the point. The point is that the jobs don't look anything like those built by our company. The reason is not that they changed anything, but the lack of quality control from selecting plants, to placement, to planting technique, to hardscape materials, to craftsmanship, .... The design was the same, the execution was not.
I have worked both of these positions. Sometimes one, Sometimes the other, and sometimes both. I can tell you that I believe that you are much more important in executing the job than in selling it at this stage of your company's life. Y
Either way, you will still have to manage whichever position you hire for. Managing a designer/sales person takes a lot less day to day time than managing a project manager.
That is what I have experienced from the view of the person being hired.
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