An aircraft company planning to start a new aircraft development program has to perform marketing, technological and economical trade-offs in order to support the decision making process. Considerations are devoted to the regional airliner market. Technologies are discussed for this class of aircraft. The commercial aspects covered concentrate on return on investment and modern cost saving production methods.But even the best prepared program has to survive certain unforeseeables, such as oil crises, natural catastrophes, the influence of terrorism, to list just a few. The final challenge is with the entrepreneur to take the last decision after serious and dedicated preparations.