Now, I must manually email Zillow to set up the syndication, wait for a response, and I've lost automation between Zillow and Tenant Cloud.

It's not a fully automated process.

For the first one, tracking expenses won't be too difficult, but I'm looking to setup processes in place to automate and streamline it to scale. 

With the Quickbooks version I use (Simple Start) they don't allow automated invoicing however I believe with the essentials & Plus versions they do allow reoccurring invoicing but I've not seen it in action.  

She has since given me access to MLS as a "listing assistant" so I can prescreeen even more.I then set up a local bank account for which she deposits the rent, and in turn automated payments to mortgage company from it for a truly handsoff investment. 

If you do use QuickBooks - ACH is only .50 cents or use an integrated software that automates everything from sending emails to applying the payments to the invoices.

By day, I'm deeply entrenched in software technical support, specializing in automation, troubleshooting, and top-notch customer service.

Automation can help.

I'm the owner of a home automation services business.

I love the automated stats and ease of generating a pdf file.