I've made a few comments in a post by Bill Kennedy that deals with the topic of switching from Top Producer to possibly Outlook. In his post and in a few of the comments, there were references to Outlook being free.
Yesterday I stumbled across an old document that reminded me of how expensive free things can be.
In the old days, I was the IT guy at a company that had about 400 PCs. When the decision to switch to Outlook was made, the 78 page document to the left was created to answer *most* of the questions that would arise. While this had been designed for users, everyone knows, most don't like to read the manual. What followed was a long bumpy ride that consumed many months of tech support to get everyone comfortable with the new and improved email system.
Granted you likely don't have 400 PCs in your office but even for one, there still can be 78 pages of things to write about adjusting from the old to the new.
But my point is not to bash Outlook. This is about switching from one thing to another. That could be converting your old website to a CMS-based version, going from Top Producer to Outlook or changing mobile phone carriers. Regardless of the initial price, they all have conversion costs that will consume your time and money.
If you're planning a conversion, take the time to write down what's required, then prioritize based on your business processes. Going from Top Producer to a plug-in enhanced version of Outlook might work, but without that list of priorities, you run the risk of learning how expensive free software can be.
There is free software too. Thunderbird is a very viable outlook replacement and could easily replace TP as well.
Also for CMS I just made my own CMS website using open source Joomla! It really wasnt that hard and is easily more content rich than a website that would take 1000's of hours to develop.
The hard part is like you said time and money. Not everything has to cost money but it does take time to learn something new. But everyone has free time and if you take a break and look over how to use something new it can be fun and exciting too.