A lot of these questions don't really have to do with ColdFusion, but could apply to any application.
What kind of documentation does the application have? What kind of indicators does it have for new builds, feature requests, change requests, etc? One nice thing about ColdFusion apps is that, generally, the source code is available for you to read, so you can start there. But there should also be other information, that might provide additional useful information. This is the kind of thing you can hire a consultant to do if you don't know how to do it yourself.
The future of ColdFusion looks pretty positive to me, right now. It's been around forever, and Adobe will keep selling as long as there's a market for it. There are lots of mature apps built in ColdFusion, and presumably new people are updating those apps regularly to add new features, etc. Adobe releases new versions about every eighteen months or so, and holds two conferences a year on ColdFusion. That said, server-side programming languages are pretty close to a commodity, and the leading edge of server-side development is probably around Node.js right now (or maybe even that has passed along to something else!) The thing that keeps CF around is the number of mostly internal applications written in it, and the inertia of converting them to something else. That's not really a bad thing, though.
CF doesn't really provide client-site-specific licensing fees. It costs what it costs, no matter where you install it. There's a decent amount of variation around how it's licensed in cloud environments, I guess.
It doesn't really have any dependencies, any more than any other server-side programming language. You need a database, and you optionally may want an external web server. It does come with a built-in web server which may be sufficient for what you need.
I'm not sure what you mean by "RPA". Do you mean screen scrapers? It doesn't matter what server-side language you use to build web pages, they all generate HTML and you can interact with them through any HTML client you like. But ideally you'd build an API and interact with that instead. CF lets you build APIs pretty easily using a variety of data formats.
I would ask the vendor for documented change history for the application, to let you know whether it's been maintained frequently. If it's worth the effort, I'd also ask a consultant who's familiar with CF to review the application code and change history, and let you know what he or she thinks of the application. We're probably talking about two to four hours of time, depending on the complexity of the application. Not to toot my own horn, but I can do this. But lots of other people can do this as well. Charlie Arehart comes to mind - he does this sort of thing all the time. I can come up with other people who can do this, or you can take a look at people who respond to things on this forum and come up with a list yourself.
Dave Watts, Eidolon LLC
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