When you are running a membership site, you will be continually running up against the same problems. You need to remember that they are easy to deal with, and that you will figure out a way to deal with them. If you can remember that, the other problems will take care of themselves.
You are going to face three basic problems when operating a membership site: Setting up, advertising, content. Setting your site up will always be the biggest problem, especially as not everyone has the skills needed to set up the site, and it can be especially hard to get the site to be exactly the way you want it to because of the communication issue.
The best solution is to talk with your designer as much as you can and to discuss every option in advance; this way, you are prepared for anything that happens, and the fewer the surprises the better. Being forewarned is always the smartest way to go. When it comes to building a site that, you are going to base a business on, the more forewarning the better so that you have as few surprises as possible.
Advertising is its own animal. You will need to devise your own smart solutions, as the advertising needs to be designed to fit your site. Ergo, the smartest solution is to point out that you may need to ignore some of the best advice in the business in order to properly advertise your site. You need to judge if the advice you are, being given is too generic or if it fits your solution, and to react accordingly.
The needs of your site may be different from someone else's, and not all solutions work for everyone. Some people like country, some like classical; Toby Keith won't work for classical, and Bach won't work for country and it's important to know if you are country or classical, a bit of both, or neither. Of course always listen accordingly. One site may do well with banner ads, and another will do well with discussion boards; it all depends on the nature of the site.
Content is something that you need to have some fun with, and will be the hardest part. Keep in mind that content can be anything, but that you need it. The smartest thing you can do is to at least debate hiring someone to do it for you. It will ensure that your membership site will have the best content that it can have, and that content will help bring members to your site, in turn helping your site to grow. If you're not sure of your ability to provide content or you lack the skills or patience, then finding someone to create it for you is the smartest thing that you can do.
However, you need to remember that you will solve the problem. If you go into the situation with that in mind, it will be so much easier to solve the problem than if you go into it not sure of whether you will solve it or not. A positive attitude will always be more successful than a doubting or negative one, and so it will always be the cornerstone of good business. Ergo, go into every situation with a positive attitude and you will be a success.