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My personal opinion: Quality. If your software is better than the free alternative, I would pay for it. Think about your target demographic. Probably professional programmers, right? (What other group of people is willing and able to buy such a specialized tool?) If you save them time and frustration, you make their jobs easier. People can justify spending ...

I have that experience, but it was 30 years ago. Back then the only source level debugger for UN*X was a thoroughly broken POS called sdb. I wrote one for myself, called cdb, and then ... suddenly I was in business: HP, Siemens, and about half of Silicon Valley. The arrival of dbx a few years later seriously impacted my business and I sold it off to Green ...

Quality is important, sure, but you also need marketing. People are not perfectly rational. They suffer from many, many cognitive biases including: The Bandwagon Effect - We're more likely to choose what other people choose ("No one ever got fired for buying IBM"). Confirmation Bias - We like to make choices that confirm what we already believe versus ...

Most Windows software is sold independently. Though if you are new to selling software often its a good idea to start off with one of the original 'app stores' - otherwise known as shareware registration services or payment processors - if you dont want to manage the sales process and downloads yourself. Depending on the nature of your software, there may ...

Find a 3rd party shareware registration/purchase service - dont try to do the ecommerce thing yourself right off the bat. If you do get a lot of sales right up front, you'll also have a lot of support for the product, and you dont want to get drawn into having to deal with any problems with your homegrown or self-hosted ecommerce system in addition if you ...

I would suggest to take one step at a time and keep your possibilities open. Perhaps start with cheap private hosting option, put a simple nice website with a link to download the file from your hoster's hard drive. Once you feel that you need more resources, just ask the hoster, they would usually provide you with a faster account (which will cost more). ...

What software tools do people pay for now? Go to their websites and see how they market them and what their customers have to say about them. Talk to people who bought them and see why they were willing to pay. Download their free versions and compare to the open source stuff you find to see why you might choose them. Do the market research required to see ...

Even if your software does the same job as a free software, if it is inherently more useful, of a better quality, and is more enjoyable to use, then people will pay for it. An example I was thinking of has already been mentioned by @PP01, Beyond Compare. I paid for this software because it is better than all of the others. Now if only it was available on ...