I saw that you're looking at bookkeeping software, including Gnucash. I've been using it for a good couple+ years and wanted to offer my thoughts. - I love it generally. Pretty easy to use double-entry system, kind of like Quicken.
- Make sure you have your accounts set up to match your tax and reporting requirements, and so that anyone putting entries in will understand which account includes what kind of expenses.
- Easy to reconcile with bank statements. It's not a "connect to my bank" kind of system like Quicken used to be (and may still be) to update your account and reconcile all at once, but if you keep up with your entries, end of month is a breeze.
- Nice reporting once you figure out what you need to know and which menu choice does it.
- It's apparently really easy to screw things up and not notice. By the end of every year I have had to go back and re-balance at least one or two of my bank statements because some transaction disappeared somewhere and balancing against a statement becomes a problem (tho' prior balances have worked out fine).
- Because of that last point, I'm considering another option this year.
j.