I've had problems with both Quicken and Mint. I was a desktop Quicken user for years, but I got sick of the “kill pills” they baked into their desktop software, which disabled the ability to connect with your bank after a couple of years. It was their way of trying to force you to upgrade. All it forced me to do was switch to a competitor's product. I switched to Moneydance, which is pretty similar, at least for what I use it for, and without the kill pill built in.

One of the several apps I looked at before switching to Moneydance was Mint, but it lacked some very basic functionality to serve as a true money management tool. At least back when I tried it out, there was no way to manually enter a transaction, so no way to know your true balance on a given day. For example, if I sent someone a check (either manually, or online via my credit union), I always enter that into Moneydance, so I know that that money isn't really available. With Mint, that will only show up after the check clears, meaning my balance could be off for several days, sometimes significantly so if I wrote several big checks. Mint also struck me as more of a planning tool, rather than a money management tool, unless something has changed since I tried it.