OK! It looks like you are very close to making your final determination about your software needs, even though it means continuing with an Intuit product.
As I understand your needs, you are looking for software that satisfies two separate functions: your home finance needs and your husband's small business needs. Historically it has been difficult to find one software package on the Mac that did a good job at both of these functions. Fifteen years ago, I used both Quicken and Quickbooks for Mac to satisfy my needs in this area, but my "business" needs ended a few years later and I stopped using QB.
Just a clarifying question, so that perhaps I can add some additional information to your mix:
What is so time consuming about making Quicken 2016 work for your needs other than invoicing?
As to your comment about your lost ability to use Quicken on Windows for downloading banking/cc charges if you did not upgrade every two years:
I am not aware of this limitation on the Mac side. That being said, I personally have made the decision, given the ever growing risk of identity theft/hacking, that I would NEVER trust any piece of software with the login/passwords for ALL of my financial accounts! What a potential nightmare the day you wake upt to tens of thousands of dollars missing from your savings account; and good luck with the time it will take to get the money back, if ever!
There is a simple workaround in Quicken (and presumably all of its competing products):
I try to use my "charge card" (that is, a card that requires me to pay 100% of the balance due each month, and is not a "credit" card) for ALL of my financial transactions. The consumer protection laws gives us much better protection from fraud on a charge/credit card, then otherwise. If the merchant will not accept that brand of charge card, then I use my "consumer credit card" which I elect then to pay off 100% every month. Finally, if required, and all else is not acceptable, I write a check, and in these ever increasingly rare instances, I manually enter this transaction into Quicken as my "checkbook register."
Every month, I go to the website for each of my three charge/credit cards (one charge card, one consumer credit card and one "gasoline" card), make the monthly payment to that card and download a QIF file of the previous month's transactions. I then manually "import" the QIF file into the register of the appropriate account and all I have to do is designate which "category" is needed for that specific transaction. I then reconcile the account against the prior month's statement.
While not as sleek as downloading all of this information, it does not add much more work/time to my monthly Quiicken needs and gives me much more peace of mind!
As QIF does not produce income for Intuit, they have been pressuring financial institutions, including my "charge card" provider, to stop providing QIF downloads from their website. To future-proof myself however: I now download this card's transactions in CSV and I purchased a CSV2QIF converter from MoneyThumb, which works quite nicely. And now I am starting my research on downloading in QFX format as an alternative.
With these thoughts in mind, and pending your answer to my question above, I do not see why Quicken 2016 cannot meet your household needs, other than invoicing.
