1. Switching web hosting.  Setting it up the first time really isn’t a big hassle.  Having to switch after you have content, protected directory structures, databases, server settings, cron jobs, mail accounts, etc. etc…. that’s a nightmare.  If you have an extensive site, it’s like moving to a new country – and I’m speaking from experience here.
   
   So what’s the solution?  Go with something reputable, stable, and with room to grow.  I know it’s difficult to picture what you might want to do in the future, but make sure you shop around.  Don’t go with your brother’s buddy who has a server at home and will host you cheap.  Don’t take up the offer of that nice guy you’ve been chatting with to host you for free.  Just don’t.  I’ve switched hosts four times over the years, and every time but the last one I cut corners, and I always regretted it.  I don’t doubt that sometimes it works out, but I’ve heard more horror stories about this than anything.
   

1. Editing/converting videos.  Okay, some people love this, but it’s been one of my biggest headaches.  My problem is that I don’t have a standard way of doing things.  I could take a movie on my laptop, or with a video camera, or with my cell phone, or with someone else’s cell phone, or with a digital camera… they all output different formats.  The software that comes with them inputs different formats.  I still have yet to find one universal tool that imports and exports everything properly.  So every time I use a new piece of equipment, or want to upload to a new location (my gallery, a blog, Hipcast, MySpace, etc.), it’s a discovery process all over again.  My advice:  try your best to stick to one format, both for the creation and the output.
   

1. Setting up billing systems.  This is just a hassle no matter what.  They need paperwork, banking details, site details… then you have to set it up on your site, get your content and permissions working right on the server, test the bejeezus out of it, and make sure you have your purchase and cancellation links right.  There are a lot of things that can go wrong.  Usually the company is quite helpful, especially for a simple site, but budget more time and money than you expect.  Accepting credit cards directly on your site is a big step.  And that brings me to #4…

1. Bending the rules for payment.  This one is such a hard lesson because both the payoff and the risk are extremely high.  What I’m talking about here is using a payment system (*cough*PayPal*cough*Stormpay) for something prohibited.  If you don’t get caught (and don’t get me wrong – many of you won’t, which is what makes it tempting), it saves you the huge hassle and expensive of #3.  If you do get caught… well, you’ll likely be out a whole lot of money without warning, and you’ll have to scramble if you want to keep accepting payments.  They will fine you, shut you down, and keep your money.  Even if you’re using an adult processor like CCBill or Verotel, read the fine print carefully – the former doesn’t allow you to sell any physical goods, and the latter doesn’t even allow you to sell services (ie. private shows).

1. Cam software.  Gah, I have never encountered an industry of more frustrating software than that used for cams.  I have a particular hatred for network camera software, which always seems to be buggy, inflexible, and not user-friendly.  Simple cam image uploading programs can work just fine, but getting multiple cams running 24/7 is a big headache.

1. Thinking you can keep your cam/site a secret.  This isn’t one that I’ve encountered personally (I’m freakishly open about my site, but I know that’s not for everyone), but it’s happened to almost everyone I know in the field.  Despite all best attempts to hide your real name, location, or work/school, chances are very high that someone you know in real life will find out about your site.  Don’t expect otherwise. 

Live and learn.  These lessons are here so that others can avoid them, or at least be aware of the risks!