Braumeister, your story is similar to mine. I started with MS Money, used it from late 90's until 2004, when they announced it would be discontinued. I then bought a copy of Quicken and gradually migrated there. I was pretty happy with Quicken. Occasional bugs, but no major issues.
I started using a Mac about a year ago and was sick of having to go to the Windows PC to use Quicken, so I bought a copy of Moneydance. At the time, the biggest selling point for me is that it's cross platform. I played around with it, but at the time I decided that I didn't want to go through the hassle of migrating over and resigned myself to paying the Quicken tax. Then I got my letter from Quicken telling me that I need to upgrade or I'll lose online functionality. I went to Amazon, thinking I'd buy the latest version, but it had terrible reviews.
So I decided to try out Moneydance. I did this at the start of the year and didn't migrate my data, except for the investment accounts. It took me a few weeks to get everything right, maybe 20-30 hours total (maybe more), at which point I stopped using Quicken. I remember migrating from MS Money to Quicken and this wasn't any worse. Fortunately, humans are adaptable creatures.
I only have two complaints about Moneydance and I think one of them is because I've been too lazy to figure it out.
The first one is that I always forecasted account balance in my primary checking account to make sure there's enough money in the account. With Moneydance, it seems to take into account the reminders, but not future dated entries already in the account. This is the one that I think I might be doing something wrong.
The other one is the portfolio reports. In Quicken (and MS Money before that), I was able to display my portfolio based on the investment, not account. For example, if I owned a Total US Market Fund in a Roth, 401k, and taxable account, with viewing by investment it's give me the total number of shares, value, etc for all the accounts combined. With Moneydance, I can only view my portfolio by account, so I have to manually add up all the shares, etc, to get the total amount (I use this data to enter in a spreadsheet, which is what I use for managing our portfolio). I looked on the Moneydance forums, but couldn't find any help. The nice thing about Moneydance though is that I should be able to write my own plugin, which should allow me to generate a custom report (still need to look into this one).