I've been a loyal Mac user almost as long as I've been diabetic. Bottom line is that if you want something that will support downloading readings from your meter, you have no options in Mac. I've tried them all, but the work of entering everything manually was just something I couldn't do - it was too time consuming.
Health Engage wasn't a bad software, but it was a Windows app that got a Mac version, and like many softwares like that it had some quirks. Most everything else is a glorified spreadsheet. But nothing will download the data.
I use a One Touch Ultra meter. I've contacted Lifescan more than once asking if or when they'll have a Mac version. The bottom line is that there simply isn't a large enough demand for it to justify the expense of developing the software. (I actually read that as "We don't really need to" but that's probably just my Mac-centered mind feeling discriminated.) That's likely the truth though if you think about it. The market for this software (outside the medical field) is rather slim, as I suspect it's more likely to be interesting to a type 1 than a type 2. Factor in the 2 to 3 million type 1s in the US, and then the roughly 10% of the market for Mac, and then the % using the specific brand of meter and you're talking ...what? If Lifescan's One Touch has even 25% of market you're only talking about 50,000 people at max, and it's likely to be significantly smaller. Software development is expensive, and it's expensive to maintain. I even tried to convince Lifetouch that if they were to develop a Mac version they'd corner the market on it - though that's faulty thinking too.
Last year I actually broke down and started looking for a used windows laptop solely for the purpose of running the One Touch software. I know, ridiculous. In the end though, I justified buying an Intel MacBook to replace my old iBook, and—although it was slightly nauseating—I purchased XP, used Boot Camp and created an XP portion. The only time I ever boot up the XP part is to download my meter, run some reports, print them (using a pdf writer) and saving those reports.
I'd say life isn't fair, but I think we all knew that already.