Customizing the System to fit your needs
For the new system to be successful for your organization it needs to be customized. Furthermore, it has to be rolled out. This means that you need to find someone who can help you do both. We're starting a new program attempting to match the best customization and deployment talent to the clients that need help implementing a system. Feel free to drop a line and we'll do the matching!~
Point application vs. a Platform
Point application (application that solves one specific problem) is usually a better way to start as it provides a quicker adoption path, there are less stakeholders to convince and can be positioned as a "proof of concept"
Platforms are necessary when the organizations get serious about rolling out the functionality.
Cloud or On Premise
That largely depends on your data sensitivity and in-house resources available to support the product. Many SaaS vendors do offer an on-premise version. One way to get started is avoid capturing sensitive information at first while running the cloud version
Generic or Industry-specific
Generic apps usually evolve faster than industry-specific ones offering better usability and cutting-edge functionality. They also usually offer better integration with other standardized systems (like PBX or Document Management). Industry-specific ones on the other hand offer better integration with industry-specific systems.
New player vs. Incumbent
Incumbent providers move slower, are usually more expensive, and what's most frustrating like to play the stalling games by promising to deliver functionality that's equivalent or better to what you're asking for in "the next release". Most often that is not true as most legacy systems were not architected to support the new functionality and end up showing up only after a major system redesign, or in with cumbersome functionality in earlier versions.