It does not have to be a one to one exchange or a asset class to asset class.

We'd even be happy to move them into one of our (future) properties and just let them keep all/most of their rent income as free cashflow. 

One thing to be aware of is the FHA multifamily self-sufficiency calculation which determines if a property can generate enough rental income to cover its mortgage payments.

2) You have one rental now, what's your goal of buying more?

The one I am current using is terrible. 

Focus on one strategy, practice analyzing deals, and take consistent small steps like attending events and building relationships.

1) I think it’s “funny” that not one news article I ever read for the last 5 years had headlines like “Housing at historical record lows!

So, Anca, your parents can 1031 from one property into more than one. 

I currently own one home in NY as LTR, one STR in SWFL but am looking to expand my portfolio.

If you don't do anything within the software, maybe only your bookkeeper needs the software and he/she can print out the reports for you.If you want access, then you and the bookkeeper would need the desktop version and possibly a shared folder like google drive to share the quickbooks file.Intuit used to sell the quickbooks desktop(one time purchase).