You should update your site as often as you have promised people that you will. For some people, once a month will be sufficient for some organizations, daily update is required. You should remove any "this site is always under construction" references as most people assume that the Web is an area where "hard hats must be worn" at all times and everyone's site is only hours, days or weeks from being updated or having a complete makeover. It's a good idea to add a "new" graphic to any new areas so regular visitors can see quickly what might have been added since they last visited. But make sure the "new" signs are down when the information is no longer fresh.
When you do update, check all your links to make sure they are current, before and after you update. You'll be surprised how many tiny errors can slip in when you update a site, so check everything is working correctly. Every site should have a major makeover every 12 to 18 months to keep abreast of changes in what's hot and what's not on the Web. When tables and frames came in, many people made over their sites using these new features, and now with Java and JavaScript support becoming more universal, you can expect to see makeovers that take advantage of these too. And for the future? Well, style sheets may be all the rage. - Updated: