The study contains the results of an informational and analytical assessment of the problems and prospects for the development of small and medium-sized enterprises (SMEs) in the regions of Ukraine (in the example of the Vinnytsia and Khmelnytskyi regions) with the involvement of various groups of stakeholders. The assessment of the potential for the development of entrepreneurship is considered as the basis for substantiating meaningful priorities of program support for SMEs as a factor in strengthening the competitiveness of the regional economy. Features of the author's methodology for conducting a study of the potential and attractiveness of the Vinnytsia and Khmelnytskyi regions with regard to the development of SMEs are presented. It includes the analysis of available statistical and informational materials obtained from official sources (office research), as well as the processing of primary information collected at the stage of sociological research (“field” research), and involves the sequential implementation of four main stages. A brief description of the key results obtained as a result of the survey of the main stakeholders (residents of the community as consumers of services and products of SMEs; local and relocated SMEs; local authorities whose powers include supporting and promoting the development of SMEs) and holding focus groups is given. The priority directions of SME development, which are relevant for both researched regions, have been determined: development of business management skills and mentoring support (business support). Modernisation of technologies and equipment; introduction of a system of preferential taxation of SMEs, solving problems of staffing. The obtained results of the information-analytical assessment of the problems and prospects of the development of SMEs in the Vinnytsia and Khmelnytskyi regions are used as a basis for the development of projects of regional entrepreneurship support programs and justification of their priorities.