May I install subscription Quicken for Mac on my iMac using my Quicken for Windows subscription?

Just to amplify a bit on Greg's post above, it's important to understand that Quicken Mac and Quicken Windows are similar programs, but not identical. (Think: close cousins, not twins.) And the databases and the file formats they use are very different.

There is a converter in Quicken Mac which can import a Quicken Windows data file. For most people, it produces a pretty clean import, but some clean-up may be required to get account balances precise. Also be aware that all your transaction data imports, but not other things like reports, budgets and attachments.

There is somewhat of a converter to export a Quicken Mac file and import it into Quicken Windows, but it existed for a previous incarnation of Quicken Mac and doesn't import all data; specifically, investment data is not imported. For most people, this translates to not having a way to go from Quicken Mac to Quicken Windows.

So if you wanted to put Quicken on your Mac to explore the feasibility of converting to the Mac going forward, yes, this is a perfect scenario. If you were looking to be able to switch back and forth between using your Mac and windows machine, no, that doesn't work.

In the latter case, you might explore whether it would work for you to plant your Quicken data file on one machine or the other, and then use the cloud-based web interface so you could enter or check data from the other machine. (The web interface doesn't contain all your data, and doesn't have all the reporting and feature of the desktop program, but can be useful if you want to enter expenses while traveling, for example.) There are other possibilities, such as using remote access software on the Mac to access your Windows computer, or installing virtual machine software on your Mac in order to run Quicken Windows on the Mac... it depends on what your usage needs will be.