I'm writing an article about what people should expect and plan for when building a new site and could use a bit of help. Here are the obsticles I can think of so far:
Budget - How much cash do you have to build the site? Then maintain, update and add to it? Promote it?
Experience - Web development isn't what it was 5 years ago. Experience for design to make sure your layout holds and experience for SEO to make sure your site gets listed and gets traffic from the SEs. Also experience to get conversions.
Discipline - Keeping on track with the development timeline and then keeping the site up-to-date. Seeing the web site as always "in progress" never complete.
Patience - Goes with discipline but sometimes sites don't do backflips right away.
Traffic - Getting traffic. Putting the URL on all your collateral (business cards, fliers, advertisements, etc.), promoting the new site, encouraging repeat visits, SEO/SEM.
Sandbox - Don't rely on G for traffic for *about* a year...
Competition - Age advantage, backlinks, and the establishment of the brand/reputation online.
Customer Base - If your customer base is *not* online or is just now getting online there are some technological limitations to keep in mind.
Anything else?