davidroetzel

Three approaches come to mind:

1) Sell professional support

This is how most open source software companies make money. This usually includes some horrendous subscription fee and guaranteed SLAs.

I never quite understood, why this works. My only explanation is, that many customers are comfortable with this, because this is what they are used to from buying proprietary software.

2) Sell a hosted version

This is classic SaaS. If you find a way to automate setup of instances of your software and offer this for an attractive price, this could appeal to people who shy away from the cost of running their own server and installing and maintaining the software.

I firmly believe that SaaS and Open Source do not contradict each other, but I only know one example that seems to be successful: http://www.teambox.com

3) Open Core

Sell a paid version of your software that has features not in the open source version. This is generally frowned upon by open source people, and rightfully so. At least you run the risk of destroying the healthy developer community you seem to have.

In your case, I would gather that you have a huge advantage when it comes to choosing the right approach. If you know who owns the hundreds of sites that already run your software then you already know some of your potential customers.

Talk to them and try to find out why they use your software, if they make any revenue of it, what their pain points are (if any) and what they would be willing to pay for.

I do not want to weigh in on the issue as a whole, but rather shed some light on an aspect you as a single coder have probably not given much thought to: accessibility and maintainability.

When I started using ruby on rails, adhering to all the conventions DHH came up with, especially the directory structure, felt like giving up a lot of control. And I, too, liked control.

But I had an epiphany when I first had to work with other people's rails code: Never before did it take me so little time to dive into and familiarize myself with someone else's code. I was productive at day one, while my customer did not really expect any results for the first 4-5 days.

So, if you ever plan on having someone else work with you on your code, or you need someone to take over maintenance of it, having a foundation that other people are already familiar with and where there is tons of documentation available, is a huge advantage.

But even if you stay alone on this project. With all you have learned, it is possible that you will approach your next project in a completely different way. In that case coming back to your old codebase in 6 months or a year will be painful. Having a consistent framework for all of your projects helps mitigate this kind of pain a lot.

regarding Ruby:

Ruby is dynamic. Kind of like Perl, Python and PHP, but meta-programming features make it feel even more powerful.

Ruby is object-oriented. Even more than, let's say, Java. No primitive data types. Even things like regular expressions and pieces of program code are objects. This makes the language feel very consistent.

Ruby is beautiful. The syntax and consistency appeal to many developers for a variety of reasons. For me it's the fact, that if you adhere to some common sense rules of naming your variables and methods you get extremely readable code.

Ruby has some unique and interesting features. Such as code blocks (kind of closures).

Combined this means that you can accomplish a lot with very small amounts of actual code. Still, this code remains extremely readable and thus maintanable.

For many developers, Ruby ist the last language they ever want to learn. But to be honest, I think it is not for everyone. You should try it and see if it feels "right" for you. Do not worry, if you don't get it, and maybe try Python instead.

regarding Rails:

Today, I guess Rails is nothing special anymore. These days you can choose from a variety of quality web frameworks in whatever language you are comfortable with (and most of those probably borrow some ideas from Rails).

To understand what really set Rails apart you have to imagine the world of web development in 2004, when Rails was first released. Back then you had to either use PHP, which has a bad reputation for many reasons I do not want to delve into, or some ridiculously complex Java framework.

Rails was (and still is) a wonderful framework that takes the tediousness out of many repetitive web development tasks. Furthermore it gives your project a structure, trying to lead you to write well-structured, testable and maintainable code.

Oh, and of course Rails is written in Ruby. Rails introduced many people to the Ruby programming language. I think it is the combination that makes it both so powerful and likeable.