posted 6 years ago
Microsoft Money was discontinued in 2008 (more or less..). At that time it was/is free if you can find a copy. It competed with Quicken.
MoneyDance isn't free, but last I looked (about 5-6 years ago) it's not crazy expensive and it is somewhat user friendly, unlike GnuCash. A the time it was actively maintained.
I use GnuCash, but it's really for accountants and those who can grok double entry bookkeeping - I'm neither, but I'm getting there. It has fairly good reporting options which allow me to list and display different types of transactions for special uses.
I have a good friend running a small plumbing biz who insists that Quickbooks, circa 1996 is the best out there. He may be right. It's a DOS program that hits all the basic stuff in a simple understandable way. The reports are somewhat limited, but everything you need to organize finance is there. You might find a copy on ebay and I'll ask him if he feels OK about sharing the install media (if he can find it - he's that kind of guy). Printing would be the big issue because by itself it won't recognize any printers around today. It has a generic Epsom mode that might work or the "box" you will run it inside on your operating system will need to feed it's print jobs to the main system for print out. IOW, although the data entry and screens, registers and reports should work no problem inside a DosBox, getting it to work fully including printing will take some fiddling. What he does in print to a file and then use another program to send that file to the printer when he needs hardcopy.
Old copies of Quicken and Quickbooks, say 3 to 10 years old can be found on ebay. They won't connect online with banks because Intuit arranged that online connectivity with banks expires three years after the software's release date. However, AFAIK, all versions _will_ import OFX files which, so far, all banks will provide as a download from "your" online banking site, the one you can reach with your browser. Thus you can load you monthly transactions into the software using OFX files and don't have to do that data entry (although there is often some "clean-up" involved, but I think that's true of any automated updates). The issue with ebay software is whether it will run w/out "activation" and whether, if it needs it, it can be activated/registered. I have had good luck with old copies of TurboTax but I haven't tried since about 2014 so don't know how that stands now.
Rufus