Out with the old, in with the new.
The saying I'm sure we've all heard, but how does this relate to Web Development? Well sometimes we've just got to give up that old treasure of ours, that old website, that old web application, that old Internet application, and especially if your business relies heavily on it. It can come at a cost to your company to upgrade however the long term return is well worth it.
Before you look at upgrading your website or application, you need to research your business and what benefits you can achieve out of new technology services. Before I continue on with this post, I would like to elaborate one thing "sometimes it's best to start over."
You can achieve a really magnificent result from your upgrade, but as most people will tell you, it's cheaper to simply buy brand new then to spend all the $'s on upgrading (especially these days). The same applies with technology, new programming features leaves older features depreciated, and normally time consuming compared to the latest.
Your upgrading and continuous work can only get you so far, but why not go for the full blow and get the latest technology, you'll get more power in less time.
On this note, I'm going to look further into Python and Ruby on Rails (for those who don't know what they are... go Google them).