A web-based tool is provided that helps a healthcare provider to prepare for a transition to an EHR system and to select an EHR system that is appropriate for the healthcare provider's practice. A server provides questionnaire webpages to the healthcare provider. The questionnaire webpages include questionnaires to be completed by the healthcare provider. The server receives responses to the questionnaires. The server can generate an EHR transition plan based on the responses. In addition, the server can generate a request for proposal (RFP). The RFP contains a description of an appropriate EHR system. The server generates the description of the appropriate EHR system based on the responses. The RFP also contains a request by the healthcare provider for a proposal to provide the appropriate EHR system to the healthcare provider. The server then sends the RFP to vendors selected by the healthcare provider.