I think the answer could be yes, but the question as stated is a bit too general. Do you have in mind specific software, or at least a specific kind of software

I think the answer could be yes, but the question as stated is a bit too general. Do you have in mind specific software, or at least a specific kind of software? I think it might work best in a specific niche, as you could become known as a go-to point for updated versions of software in that area. One possible way of picking software would be to try to find cases where companies are running old OSs solely to keep some legacy software operating. I know this is relatively common with some laboratory equipment, for example, where some labs are running old Win9x boxes for data collection, because the data-collection software and drivers for discontinued equipment haven't been released in a newer version.