Where should I take this Access application?

Access will be around for a long time because it is part of Microsoft Office. I think you need to look at your future developers and current users to decide whether or not to keep the data in Access. For example, you mentioned adding payment information accounting. The accountants where I work keep everything in Excel, and I help them occasionally by importing Excel spreadsheets into Access, crunching them, and then exporting the results back to Excel. I know that it plays well with Excel, and I hear that it plays well with other Office apps. You also said that it is a volunteer activity tracking system and that you don't have much Microsoft experience, so I'm guessing you and the future developers are volunteers. I think you will find a bigger pool of Access people than say, VB.NET or Unix people. It may not be "cool" but it will be "familiar" and "easy." If the application is relatively simple, you can even use people who have taken Access in school but don't have work experience. (For me, VB.NET has a steeper learning curve.) Access databases can also link to SQL Server tables, and can be converted to SQL Server databases fairly easily. Where Access falls short is in handling multiple concurrent users and in handling huge numbers of records. I don't think Access is stagnant, just limited to small operations. Microsoft hopes that if you need to escape, that you escape up to Microsoft SQL Server, and it has tried to make that path easy. Hope that helps.