Old DOS applications? No offense, but there are infinitely better solutions out there. Moving information over isn't too hard.
LOL - try telling that to a small banking institution that doesn't have an IT budget. Are there better solutions? Yes. That doesn't always make the transition cost-effective, though. Would you really pay for hundreds or thousands of man-hours to transcribe 20+ years of business records into a new database that's only marginally faster and doesn't offer any significant improvements besides for a prettier user interface? (Don't forget - whoever you give the transcription task to will probably complain endlessly about doing something new, or at least mess things up a few dozen times before getting the hang of it.)
Yes, those types of things can be automated, but hiring someone to write a program to migrate your data will usually cost more than doing the work by hand. (Not to mention you're paying custom development prices for a piece of software you'll probably only use once or twice, and then never have a need for it again.) If your business were big enough to justify such an expense, you probably would've been upgrading your equipment more frequently anyways, or at least have an in-house guy that could do the job for cheaper. And don't forget that most of these quirky little business applications were written before software companies were ubiquitous necessities, before computer programmers worried about ease of use for laymen, and well before you actually needed a real computer science education to make money doing programming. (Really, that last one isn't even entirely true these days - a lot of amateur, fundamentally flawed kludges still get passed off as commercially viable software.)
There's an increasingly wide gap between the theoretical capacity of computers and their application in the real world. I'd say roughly 95% of people who use computers for work don't actually need them at all (let alone understand how to use them efficiently.) Those folks probably wouldn't even know how to find an alternative to their outdated programs, let alone make the transition. And then there's the issue of retraining your staff to use the new software, which probably looks entirely different to them and is extremely intimidated. Even if you can afford the retraining, there will be a significant portion of the staff that complains about how the new software is too hard and makes their work slow.
Working tech support, I've met PhDs that can't even manage their own files. One of the most common problems that I help people with - people that make ten to fifteen times the money I make - is finding their MS Office files, because they don't know how to open a file if Word doesn't automatically open to the one directory where they save everything (usually the desktop or their My Documents directory.) If the Open dialog pops up and happens to have defaulted to a different location than usual, they're helpless. They call our office and start yelling about how Office lost their syllabus - usual in totally convoluted terms like, "All my files were deleted and I think it's a virus!" I've met someone with multiple doctorates in hard theoretical science that was trying to draw axes on a graph using Photoshop - a graph that they generated
in a scientific graphic application, that they use daily, that automatically labels graphs unless you specifically tell it not to. When I mentioned that they could just go back into Mathematica and get the desired result in one step, this person literally screamed into the phone that Photoshop
must be a useless, inferior piece of junk software because it can't draw straight lines like Powerpoint or MS Paint, and then hung up on me.
Basically, my point is that you're totally right - but being computer savvy gives you a very distorted view of computers in practice.
~Joe