If you want to avoid this you can certainly just 'gift' them the asset and they can deed it into their Trust but I doubt you want to do that without any financial exchange. - thing that you'll want to think about is the step us basis and what this sale would mean for you when they pass?

You should speak with a financial advisor about your complete financial picture before retiring overseas.

Of course I keep entities separate in all legal and financial aspects. 

This feature and the financial reporting piece of it really saved my life!!

Yes the financial benefit is attempting, but I do want to understand all the legal consequences, including insurance issues before making a decision.

You are playing with fire with this strategy to start, but then when you count in an inexperienced rehab to rent a year later, I would earmark this for disaster.

Great tools that get updated regularly.I am on the lending side of things and would be happy to hop on a call with you anytime to discuss financial strategies and help answer any questions you may have about nearly any loan product available to help you on your journey, even if they are not products my capital partners offer.We are all here to help you learn and grow.

Consistent with the advice of @Jo Bradley , if I could get through the first couple years financially, keeping current home seems a lot easier than long distance investing...and at least I know what is wrong with my current home (I.e it will eventually need new roof etc). 

This way, Tenant A gets a little financial "help" beyond their actual expenses and for Tenant B, it's a total choice to take advantage of a W/D or not.

He is an electrician and lost money that had a big impact on his life, set his family back a few years financially, prevented them from being able to buy the house they wanted to for themselves to live in, caused a lot of stress in their relationship etc.