Several questions relating to subscribing to Quicken and using on both Mac and Windows

splasher said:

#2 The Win & Mac programs use different format of data files and are NOT interchangeable.  There is a Win->Mac conversion process, but it does not convert investment accounts.

The Mac->Win conversion process does not work properly at all.

I agree with the first and last sentence but not the middle one. My understanding is that investment accounts do transfer from Quicken Windows to Quicken Mac. Many, many people report having successfully made this transition. But, as noted, you can't go the other way. And the files aren't interoperable.

If you want to use Quicken on both computers, you may want to consider installing it on one or the other and then using a screen sharing utility to allow you to access it from the other computer.

Alternatively, you can use Quicken's cloud (mobile) services to allow Quicken to sync your desktop data to its cloud servers, and then access that data via a web interface. (Note that while this is not new or unproven technology, it an area where users sometimes run into problems with the sync process.)

ddschur said:

2. How difficult and what do you suggest as to how to convert the current Quicken file to be able to use it and open on the new Mac?

Since you already have the Mac, once you purchase a Quicken subscription, you'll be able to download it for both your Windows computer and you're Mac. The best way to see if you have conversion problems is to try it yourself with your own data. Some people who have made the transition will tell you it was perfect and seamless. Some will say it worked pretty well for them, but they had to do some cleanup to get their account balances correct. A smaller number will tell you they hit a major problem and weren't able to successfully convert. So try it and see how it goes with your data file. You can do a conversion and play with it as a test to see how clean everything is and to start the learning curve of Quicken Mac while continuing to use it on your Windows machine; then, if/when you decide you want to switch to the Mac, convert the file again and use it on the Mac going forward.

ddschur said:

3. I would like to purchase the Deluxe version of the subscription service but I noticed that one of the differences is that in Deluxe it doesn't allow for IRS Schedule B (Dividends and Interest) to be used in Deluxe...question is will that affect importing, etc. to TurboTax?; and,

I can only answer this for Quicken Mac. Answer: the comparison chart is flat-out wrong! I and others have pointed this out to Quicken folks numerous times, but they haven't fixed the chart. The Quicken Mac Tax Schedule Report absolutely does show Schedule B dividends and interest. This report exists in the Deluxe version.

ddschur said:

4. When the conversion is requested for the file from Windows to Mac, will the current settings and views but ported over to the new versions?

As @splasher said above, only your data will transfer, not specific settings; the two programs are different enough, and the Mac version has been evolving over the years, so they never tried to map settings, preferences, etc. from one to the other. You will also lose your saved reports and need to re-create them. If you use the budget, you will need to re-create your budget in Quicken Mac. And if you have attachments, they will not migrate in the conversion.

Follow the few preparatory steps mentioned on this Quicken Support page to make the conversion.