Reader Donald Kaye is in the same boat as many old-time Mac users and recent switchers. He writes:
A major problem will exist next month when Lion is released for me and I presume many others. I've updated my operating system with each new release but this might be the first time I don't. The problem is Quicken. I use an older version of the program because I'm unhappy with the current version, but this old version won't run because it requires Rosetta, which isn't supported in Lion. What can I do?
This is going to be a problem for a lot of people who rely on software that, in turn, relies on Rosetta. Broadly, you have a couple of options. One is to create a dual-boot Mac--one that can boot from two volumes. One volume contains Lion and another runs an older version of the Mac OS. When you need to spend some quality Rosetta time, you boot into the older OS. And yes, this is a pain.
The other option is to simply not update to Lion. Your Mac will continue to work just as well as it does today. How acceptable this is to you depends on how desperate you are for Lion's features and iCloud (some of iCloud's features will require Lion).
One other option, I suppose, is to rail against Apple for dropping Rosetta with Lion. But, quite honestly, you then join the ranks of HyperCard and AppleWorks devotees who share their devotion for these applications with a passion for tilting at windmills.
Specific to your Quicken issue, how about this "what are you thinking?" advice: Have you considered running Windows on your Mac? I can't recall ever offering such advice, but I've come to the conclusion that if you want to run a full-featured version of Quicken, you use the Windows variety. Intuit appears to have a deathly fear of making a version of Quicken for the Mac that exactly matches the features of its Windows counterpart. So why struggle? As I've suggested to friends who've recently switched to the Mac from Windows, if you want to run a reliable and full-featured version of Quicken, do so under Windows--either in a Boot Camp partition or using virtualization software such as Parallels Desktop For Mac or VMware Fusion.
Yes, it means acquiring a copy of Windows and yet another copy of Quicken, but it does provide you with a version of Quicken that's more feature-packed than the one Intuit's shipping for the Mac, you're likely to get new features sooner with a Windows version, and, unlike with your current situation, your copy of the application won't go the way of the dodo because of an operating system upgrade.