This is probably the one area where the Mac is chronically weak; although some people will argue the point.
If you only used the very basic features of MS Money (a checking account, credit card and maybe a few shares), something like iBank might suit. However iBank has some very serious problems (if you don't believe me, go to their forums and take a look - I post there regularly under the same username). iBank does direct downloads (although not for securities), has some OK graphs and reports (although not net worth, or balances over time) and it really looks stunning (apart from the columns going out of alighment or vanishing altogether). The biggest issue with iBank is that the releases are very rare and you never know if your feature or fix will make it. Also the reconcile feature stinks (there is a thread about this on their forums) and the input interface has a nice selection of bugs.
MyMoney (mthbuilt.com)is another alternative, but it's still undergoing development and for me lacks too many basic features (budgeting and securities for a start). However they ARE on their way, and unlike iBank you can talk to the developers directly on the forums and they really do listen.
MoneyWell (nothirst.com) is also looking better. The workflow is horrible (you have to allocate cash flows and then withdraw money from buckets) and it excludes securities, but 1.4 (still in beta) supports direct downloads, which is nice.
Moneydance is a cross-platform alternative. Some people like it, but for me it's the worst of both worlds. It lacks the functionality of MS Money and lacks the looks of iBank. Also the import and reconcile features are really painful; you have to agree each and every transaction when reconciling (yawn).
Money 3, Squirel 0.5.7, Chekbook, Liquid Ledger and others, all offer some nice features, interesting interfaces and varying levels of support (from none to almost none). However they all lack direct downloads... this doesn't bother some people, but if like me you have 4 credit cards including corporate ones, bank accounts in several currencies, a stock portfolio you like to have updated daily, or even hourly, and care in wny way whatsoever about understanding your net worth etc, these are 'toy' applications at best.
Finally Quicken for Mac. Now, if you had never used a PC, or PC Quicken, you might think the Mac version was quite good (if you don't mind applications that looks like they were developed on OS 8.5). However, it's slow, full of bugs, is missing features that were in Quicken 1999 on PC (such as multi-currency, the ability to skip a single payment or make overpayments on loans etc), and even worse, Intuit have all but forgotten about support (again check the forums at intuit).
The only ray of hope is Quicken Life for Mac, which is due this Autumn. The beta should have already started, but things have gone quiet, but it's supposed to be a brand new financial app for the mac. However it is not expected to be feature complete (although Quicken Mac never was either) and no one really knows when it will be released, if at all.
Honestly, the best advice, is to install MS Money on your Mac via Parallels or VM Fusion (you could buy either for the same price as iBank). It will save you a lot of grey hairs, believe me.
Honestly, I have downloaded just about EVERY financial app available for the Mac, and not one of them even comes remotely close to MS Money 2002, much less anything released in the last 2 years, which is a real shame. There is an opportunity for anyone who wants to bring this type of app to the Mac. I only keep my Windows install for MS Money, which says a lot, and my poor MacBook is a 2006 model, with only 2GBs of RAM - so this is a big sacrifice for me when I am updating my finances. I would not take the decision or advice lightly.
