Why not setup a web application, and host everything on your servers? Then, offer different plans based on the amount of work they're receiving. This is the be

Why not setup a web application, and host everything on your servers? Then, offer different plans based on the amount of work they're receiving. This is the beauty of web applications, they don't need to run their own hosting, manage a VPS, or register a domain. I think that would be overwhelming for non-profit art organizations, so if you can get them started in minutes with a few clicks, you'll be more likely to win them over. Customizing software for each organization seems like a nightmare, along with the support to follow. If they're hosting things on their own, you'll have to troubleshoot that as well. You might make more money per organization, but I think you'll reach far less. You said the core of the software is fairly simple, and some groups don't need anything too complex. Start there, get the core of the software working, and get something online. Approach these groups, get feedback, get them signed up, and start growing. When you have a few customers, you can start adding more features, and building out the software. Don't try to build a monster app all at once, you'll end up over your head, get frustrated, lose interest, and be less likely to ever finish. Remember, everything takes far longer than expected. Keep it simple to start.