Outside of the cost considerations (do I want to pay a monthly fee or a large amount up front and hopefully less in maintenance in the future) there are other key factors in deciding which path to go down.
Here are a few other considerations before making the leap.
In-house technical ability
If you are running your own servers and have business-critical applications on these servers, you need staff dedicated to ensuring their function is aligned to the business' requirements and that if users have problems with the application, these staff can assist them. One of the key reasons I see CRM implementations fail is a CRM system is implemented and then falls into disrepair as no one within the company is tasked with championing its use or continually improving it.
Business attitude to information
Some businesses are fearful of housing their data outside of the four walls of their business. There is no wrong or right answer to this and it is simply something the business must consider.
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