When you have the conversation - Have a discussion to see what the tax would be on an outright sale.You may have suspended passive losses that would eat up most of your gain.If the property was previously a personal residence, there may be some exclusion.If you do have a gain upon sale, have a conversation to see what options(if any) you have of deferring the gain and what the steps would be.

Also, good investor insurance providers will also offer a loss of rents rider at no additional charge.

Loss potential- $50,0002. 

We root for each other and learn from our wins, losses, etc.

However, there are plenty of great freehold properties in Costa Rica so buying leasehold there makes no sense to me.I'd only buy that property if I absolutely have to have that one and if the enjoyment I get from it until the current term of the concession ends is greater than the pain I could get from the potential loss of my investment.I didn't mean to poop the party but, whatever you decide to do, it's good to be aware that that risk isn't non-existent, as your lawyer seems to be suggesting.

My parents were and still are invested in both SF & MF property in BC so I have seen some behind the scenes of the ups and downs of managing apartment buildings, tenant grow ops in basements, capital gains and losses. 

I have had clients use them for mutliple types of losses and they've done an excellent job for the clients.

Here’s the risk involved with that:If the market drops when you want to pull the money then you either accept the loss or are limited to using your own saved capital instead.The money is slightly less accessible. 

The loss of control was strange, I will admit.

Actual loss would be more if I consider CapEx,vacancy, maintenance etc.But, my goal as a first property purchase is also not to focus on cashflow, but instead direct my rent payments to a mortgage while getting back any extra profits from appreciation and equity built from house hacking.In San Diego, If I house hack a condo, with a very low down-payment, I see that I'd have to spend 1000$ more than I would, while renting.