Quickbooks has gotten expensive and I'm considering just using Stessa and then sharing the reports with my CPA at the end of the year.

This is going to take many conversations with real estate lawyers, and a CPA.

This post does not create an attorney-client or CPA-client relationship.

I would recommend speaking with another CPA.  

@Joseph Hammel,It is your rental business so it is up to you who manages your properties and how much you pay, but I would suggest that you discuss this strategy with your CPA to ensure that you are fully understand all the numbers. 

So the mortgage companies and the IRS set the exact same threshold for being a second home or being a an investment property.My CPA however has advised me that there are caveats for doing repairs, or periodically visiting to inspect it, that allow you to exceed the 14 day leisure limit.

@Rory SweeneyI personally use Buildium in partnership with my CPA and book keeper!

More money than I care to say out loud to a CPA who takes the piles and piles of reports and documents I generate from all this, plus my W2 and my wife's W2, and turns it into something that the IRS will accept.

So, if you are a CPA with international/cross-border knowledge please let me know, I would love to connect.

What does your CPA say?