Has anyone had experience with this type of transaction?

It is typically your primary job.The 40 hr/week W-2 worker is going to have a hard time convincing an IRS agent they are meeting this threshold.STR loophole is a better path for my friends in this category.Once you finally cross the pro hurdle, you're not done!

Keeping fingers crossed for a sweet new tool to add to the investor belt! 

Truth time: I suspect the reason you didn't get any responses back from these alleged "wholesalers and investors" is that hardly any of them are actually transacting deals!

Will it match the statement amount up with the actual credit transaction for the bank account attached to Stessa?

While passive rental income is possible, managing it across borders can be tricky and may incur extra costs like foreigner withholding taxes and specialized tax filing.Financial Accounts (Roth IRA and HYSA): From what I understand, if you were to leave the U.S. without citizenship or a green card, your ability to contribute to a Roth IRA would be affected as you would likely no longer have U.S.

Right now we are not selling anything or cashing out that equity - if anything I would look to acquire a property and find a HML that would cross collateralize one of my other assets so I don’t have to sell it but use it as collateral.

Selling your property now will incur commission fees, so you’ll take additional losses on the transaction.

After a transformation, I import information from Stessa (it auto-injects info from banks) into a relational database, run a few queries, and then do a cross-tab query to bring it all together into a report. 

I've only experienced this on the buy-side of multifamily acquisitions, but have been involved in transactions where the lender requires a CofO and they have gotten comfortable with just the I-card, when there is no CofO for the property.