What we have are HMLs with very limited legal and compliance experience giving advice.

If I did this I would probably hire a property manager in Canada to keep me in compliance with CRA regulations.

If so, then they're just maintaining compliance with Fannie/Freddie underwriting standards.Bottom line, if you believe the risk of the loan being called down the road is outweighed by the asset protection benefit, then you don't ask, you just do it.

State laws do vary and you need blue sky compliance, but most competent securities attorneys can help with that.  

Aside from the legal and compliance issues involved, if an IRS auditor requested bank and credit card statements, why needlessly expose your personal transactions?

It’s not easy to abide by every law, it might even be impossible when compliance with some laws encourages breaking others.  

It can be pricey to reach Section 8 compliancy The Section 8 code is strict and is subject to the inspector’s perspective.

Since they are processing the transaction, they have a regulatory and compliance obligation to actually look at all the documents to ensure that they can document what is being transacted.  

The responsibility for compliance with IRS guidelines falls on the investor, which is why you want to have experts on your side.  

You think as long as I reach out to the closing company at the beginning of the process they will be able to put the deal together in compliance?