Migration to Mac.

1) Yes, Quicken Mac and Quicken Windows are independent. You can have them both download transactions from the same institutions without problem or interference with each other.

2) Yes, with the caveat that data migrations are generally clean but occasionally are not. There are many thousands of Quicken windows users who have migrated to Quicken Mac, and investment transactions do generally transfer correctly. Do you have a current Quicken subscription for your Windows PC? If so, since it sounds like you have a Mac now as well as your old Windows PC, the best thing you can do is to install Quicken Mac — it's included in your subscription at no extra fee — do a test conversion of your data, and do some comparison between the two to see what discrepancies or problems you might have. Sometimes, it's a simple matter of deleting a placeholder transaction Quicken create, or adjusting an opening balance transaction. Sometimes there can be minor discrepancies in share holdings curie to rounding differences between the platforms. While most people have generally smooth data migrations, you can judge for yourself by trying it.

3) Quicken for Mac never had a "Business & Personal" (formerly "Home & Business") version until the end of last year. The version released then laid a foundation for creating companies and business categories, but lacked invoicing capabilities. The developers issued assurances that work on the business features was ongoing, and that invoicing was definitely planned. But when? Partway through this year, the developers sought public input on what features users needed/expected, indicating they were advancing in the design of more robust business features. And then it's been silent on this front for a number of months, which is likely a sign that the programmers had their heads down and were working of building the promised new functionality. Quicken will never say when new features will be released, because the schedule changes as priories shift and as unexpected problems are encountered. So none of us can say for sure when invoicing functionality will be released, but based on the events and elapsed time in this case, I would expect it to be fairly soon (e.g. within months, not years).

@Chris_QPW said: On the business side, I'm actually a bit amazed that the conversion can be done based on my limited knowledge of how both of the systems work.

Thanks for pointing that out. I didn't think about the business-specific features when I replied above. As noted, the business features which currently exist for Quicken Mac are new within the past year, and I have no idea how the data that's specific to Business & Personal currently transfers from Windows to Mac. I can't recall if I've seen any posts about this. And with more significant business features (clients, invoices, payments, etc.) on the way, we just don't know if the developers have conversion of such data integrated into what they are building. We don't know if what they are building is based on what exists in Quicken Windows or whether it's a clean sheet new design.

@Trimedia By trying to convert your Windows data file onto your Mac, you've got little to lose except some of your time. 😂

I want to note that the are differences — some small, some large — in the way Quicken Mac and Quicken Windows look and operate. Even with all your Quicken experience, there will be a bit of a learning curve to figure out out Quicken Mac's ins and outs, and to retrain your brain to do some things differently. My advice is to do this with an open a mind as you can; if you growl or curse every time something isn't where it was on Quicken Windows, or that Quicken Mac does a little differently, you will be destined for frustration and failure. In other words, instead of "this isn't the way it worked in Quicken Windows!" if you can frame things more as "this is what I'm used to doing in Quicken Windows; how do I accomplish that in Quicken Mac?" you will adapt faster and hopefully in the end make a successful transition. Best of luck!

@Chris_QPW I think it's logical that some of the services you mentioned aren't carried over in a migration from Quicken Windows to Quicken Mac. And it's not onerous to re-enable Zillow integration, for example. (FYI, credit scores isn't a feature in Quicken Mac. Since many credit card website now provide this information, I'm not sure how missed it is in Quicken Mac; I don't recall users clamoring for it.) Even if it's necessary to re-establish downloads from financial institutions, that's generally a one-time task that's not too problematic.

The feature mentioned above — recurring scheduled online bill payments — is the only one I'm aware of where a user needs to sever the connection (delete the recurring payments) before doing the Windows → Mac migration. It seems to not be a big problem for a user who has a handful of such payments, but a significant pain for a user who has dozens of such payments. Or problematic for a user whose Windows PC has died and who decides to get a Mac and import their Windows data file. Or, like the user here, someone who wants to migrate their Windows data to Quicken Mac but to continue to use Quicken Windows in parallel for a while.

In any case, I'm glad the Quicken Mac conversion process detects this situation and warns users exactly what they need to do to avoid problems.