Having been in senior management and a CEO for many years, I have found that delegating is not only a skill but also an art. You question is very interesting as I assume that in most situations you would be delegating to people more skilled or more knowledgeable about the task or project than you are. A good manager knows their limitations and their role which is to manage rather than do. Therefore the rules on good delegation techniques still apply:

1. Identify the right person or team with the right skills and experience to do the work. It sounds as if you have done this. Write down the reasons that you feel that they will be better placed to get the best results and portray this to the person up front.
2. Be clear on the level of delegation that you are giving to them. There are 9 levels (if you would like to know these, please let me know). This includes a detailed briefing to outline the tasks/outcomes.
3. Negotiate the timeframe, reporting and results. Don't tell, ask - then double the time they estimate. Most of us underestimate the time anything will take. By providing the person with extra time they will feel much more positive about the tasks and be confident on delivering the outcome.

Negotiating the timeframe, reporting and results is the most important step. Never dictate this as you really want a good outcome and this will only be achieved if they are part of this decision.

Please call me if you would like some more practical help.

It does sound like you need to get back to your USP - who do you help, why you help them and why they should pick you. There are many different types of copywriters and the first question they should ask you is "What do you want your website to achieve"? Any copywriter worth their fee would want to know about this before starting the work.

Always protect the "core" of your business. It really doesn't matter who the developers are. Your first responsibility is to ensure that whoever is writing the source code has a strong and long term relationship with you and your business.

Take the selection process very seriously and check referees, talk to previous clients or employers and complete due diligence very thoroughly. Good coders, for example, should make plenty of comments within the script so that anyone who comes after can pick it up and run with it quickly. I have seen many businesses suffer because of a fall out with the coder who didn't do this. A new coder comes in and wants to rewrite!

I agree it really depends on what you are trying to achieve. It can take sometime to source the right person to do the job. I disagree that you should only outsource to a freelancer if you have a one off project. My designer is a freelancer and I have been using her for several years because I like her style and she is very fast and efficient so I end up paying a lot less for the work and there is usually very few edits.

I think that for any business it is worthwhile investing in creating a good relationship with any member of your team. If the work you required isn't a full time role, then hiring a freelancer makes a lot of sense because you can build a loyal and trusting relationship with them and therefore depend on them to deliver.