Quickbooks to Quicken?

If you want something that's entirely online similar to QuickBooks then you'll want to use Quicken Simplifi. They have a Business & Personal subscription level for that as well as their own forums, so if you think that's what you want you'd be better off asking about Simplifi over there.

Quicken Classic runs on your Mac; you would need the Business & Personal subscription to get access to business features. There's an option to sync your accounts to the cloud so you can access them on line or from a mobile app but I don't know how well that works with the business features; you might be restricted to accessing your business accounts on your Mac. It doesn't have any features specifically related to renting houses, but you can set up multiple businesses so you could keep the accounts for each house & business separate. There are business reports including profitability and income statements, but it does not generate 1099s.

If I'm not mistaken, Quicken Windows has some specific features related to managing rental properties like keeping track of tenants & rent for each property; those features have not made it into Quicken Mac yet.

@jacobs Can Quicken Mac create a New Worth report that is restricted to a set of tags?

No. Just conceptually, they don't go together. Net Worth reports on account balances as of a specified date. Tags are on transactions.

A net worth report would be functionally good enough for a balance sheet if there are separate accounts for each business. If funds from different businesses are commingled in accounts, I'm not sure how you'd generate separate balance sheets for each business.

@AnotherUserNameHere As I wrote above, if you have a separate Quicken data file for each business — which would indicate you have separate bank accounts, credit cards, etc. — for each business, then Quicken's Net Worth report is a reasonable alternative to a balance sheet. It would show your assets and your liabilities; your account would need to fill in the small missing equity piece (e.g. retained earnings + net profit).

@Chris_QPW I'm still trying to wrap my head around a balance sheet based on transactions limited by tag. It just doesn't make sense to me from an accounting standpoint, irrespective of what Quicken can or can't do. Again, a balance sheet shows the balance for each account: assets like checking account balance, liabilities like credit card balance, as well as assets like receivables and liabilities like sales taxes due. How would it work to include only transactions using certain tags? For a checking account, for instance, would it calculate a sum of all deposit and withdrawal transactions with the selected tags and report it as the fake balance or net worth for the checking account as of the ending date?

In Quicken Mac, you can only specify which accounts to use in a Net Worth report, and that doesn't seem like a limitation in Quicien Mac; it seems fundamentally correct to me. What am I missing?

I have only used Quicken Windows Business for a short time in a beta, it is easy to see that tags are fundamental to how it separates out businesses (you have "business tags").

Quicken Mac doesn't use that approach. You can create one or more businesses, and reporting can be for one or more or all businesses. Income, expenses, and invoices can be assigned to any business. Perhaps you can think of it as some form of super tags, but it's implemented as a separate and important field in the database. Actual Tags are the same as in non-business editions of Quicken Mac or Quicken Windows, and are completely optional on business transactions.