Well, it was announced several years ago that DOS was no longer going to be supported and that was before Windows 7 came out. Not many people actually keep up with computer news and never knew that.
DOS got pulled starting with Windows 8. Windows 7 has limited support for older DOS programs and there are quite a few that won't run.
Now, with that being said, do you actually need Internet access with a computer that you use your old DOS programs on? Ask yourself that and the updates that come across are 99.9% security updates for Internet access. If you have an old machine right now
with all of your old DOS programs, just pull the network cable from it and run it off-line. That machine should run almost forever or until the hardware gives out.
You can still get a Surface Pro model and start anew with newer programs. You can gradually migrate from the old system to the new one at your own pace. Granted, there is no export capability with your older programs, so you will need to create a starting
point and go from there - especially with personal finance programs. I do that myself.
I had found a personal finance program that is a little like Microsoft Money that works on all platforms (Windows, OS/X, and Linux) called "Money Manager EX" or "MMEX" for short. You can go here if you want to check it out: http://www.codelathe.com/mmex/mmex\_screenshots.php
It is not a perfect program but is reliable and if you upgrade the program or use a different system, all use the exact same database. I have all three platforms myself and just load up the exact same database file.
That is an example.