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I want something SIMPLE and if possible free. Paid is OK too and in this case a one time fee is prefered instead of a subscription.

I don't mind cloud apps as long as I can export my data and have a hard copy of it. I prefer to have an actual app on my computer though.

Here’s what I want to do:

  1. Be able to enter an invoice and know when it was paid. Basically keep track of unpaid invoices.
  2. Track business and personal expenses separately.
  3. Generate some sort of report to be able to send to my accountant when the time arrives. Needs to be able to break out GST for business expenses. GST is a Canadian tax (5%). This can be very simple.

Nice to have:

  • Runs in OSX.
  • App that will let me snap a pic of a purchase and link it to an expense so that when I see the bank statement and go "wtf?!" I can refer to the pic and know exactly what the charge was about.
  • Be able to be used by two separate users so that my wife can keep her business expenses separate (maybe this will require an extra license depending on the software).

I have almost no experience with software like this so suggestions on an alternative workflow are welcome (eg. use different software for personal/business stuff, etc).

  • For business invoices I've been very happy with Fresh Books. – aparente001 May 14 '17 at 22:57
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I would suggest taking a look at GNU Cash.

  • Free, Gratis & Open Source, no licence fees.
  • Multiple Accounts and Users
  • Runs on your computer but you can export/backup data in a number of formats
  • Runs on OS-X, Linux & Windows
  • Can handle tax issues
  • Can tell when an invoice was paid, etc.
  • Has an Android app that can let you capture expenses out and about for later import.
  • Export end of year reports for the accountant
  • Lots of other goodies.
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A great software that is useful for tracking expenses and invoices is Billbeez. All you have to do is e-mail over your bills/receipts and they give you a real time overview of your financials organized online along with alerts for missing and unpaid bills. https://billbeez.com/?utm_source=stack_exchange&utm_medium=blog&utm_campaign=traffic

(Disclosure: I work in business bevelopment for Billbeez)

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