Is not a Windows app, is a server microservice so I have to discard my favorite Dolphin Smalltalk for the remarkable Pharo or Squeak. Since is a business thing that will run on some linux server, I think that we'll go for Pharo. To be honest at this point Gemstone is not discarded, but geez I wish would be easier to do devops with it. A good how-to from zero to hero on a basic gemstone dev setup and minimal production setup would be so cool to have
Dolphin is a very nice Smalltalk. For business, local clients all use Windows and do not trust web apps for core applications. So Dolphin + ODBC is my latest go to for business apps.