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If people don't want to manually enter in transactions, they're not interested in personal finance, they want a fire and forget solution that tells them if they have enough money to buy something.

The reason that people need to manually enter in transactions is to they understand the operating balance, not the physical balance. When I pay my mortgage, there's a delay from when I submit the request to the lender to when the lender draws the money. For the duration of those days, the money may be in the account, but I need to ensure my finances take that into account. Otherwise, I'll submit a transaction, forget about, then buy something, and run into a bounced check or overdraft fee.

If people don't want to manually enter IP addresses, they're not internet in web browsing, they want a fire and forget solution that shows them cat pictures.

I disagree. I don't care about a difference of a few days one way or the other, because I keep enough cash in my checking account that I'm never in danger of bouncing a check or not having money for a big purchase. However, I do care about my finances.

For example, I often examine my spending over a period of a few months to see how I'm spending my money and decide whether I want to make adjustments to my spending habits or budgeting. I can (and sometimes do) do this by exporting a CSV from my bank's website, but I like the convenience of using tools like Mint and letting them auto-categorize my transactions.

It's almost as if... different people use financial tracking software in different ways!

To me, not connecting to bank account(s) is a deal breaker, and I would have no use for such a product. I've used (and suffered with) Quicken for years and years because 1) it connects and downloads from every bank/investment account I have ever had, 2) its interface is bearable, and 3) my data is stored offline. I probably use about 2% of Quicken's features, but I can't do without them. I don't use any of the budgeting features, the bill pay features, the integration with tax software, etc. I just want to get a big picture overview of my accounts, watch for fraudulent transactions, and not worry that my all my data is online and ready to be compromised or lost.

If there was an alternative to Quicken that satisfied the above 3 requirements, I'd consider switching, and I would definitely be willing pay for such software.

I don't think that's true at all. Manually entering in transactions is error prone, time consuming, and most importantly, boring as fuck. Especially because machines can do it for us.

Not wanting to do the boring, not needed stuff does not mean that I'm not interested in personal finance, and don't want to know where my money is going.

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