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. 

I made my parents some money on their retirement funds, and was able to recover approx 93% of all funds invested.

So not much of loss on their part unless the lease has 11 months left.I am interested to see what others have to say.

In reference to @Peter Walther post about foreclosure, the following is copy & pasted directly from the State Bar of Wisconsin Form 11-2003 Land Contract:"Purchaser agrees that in the event of a default in the payment of principal or interest which continues for a period ofdays following the due date or a default in performance of any other obligation of Purchaser which continuesfor a period of days following written notice thereof by Vendor (delivered personally or mailed by certifiedmail), the entire outstanding balance under this contract shall become immediately due and payable at Vendor's optionand without notice (which Purchaser hereby waives), and Vendor may singly, alternatively or in combination: (i)terminate this Contract and either recover the Property through strict foreclosure or have the Property sold by foreclosuresale; in either event, with a period of redemption, in the court's discretion, to be conditioned on full payment of the entireoutstanding balance, with interest thereon from the date of default and other amounts due hereunder (failing which allamounts previously paid by Purchaser shall be forfeited as liquidated damages for failure to fulfill this Contract and asrental for the Property); (ii) sue for specific performance of this Contract; (iii) sue for the unpaid purchase price or anyportion thereof; (iv) declare this Contract at an end and remove this Contract as a cloud on title in a quiet-title action if theequitable interest of Purchaser is insignificant; (v) have Purchaser ejected from possession of the Property and have areceiver appointed to collect any rents, issues or profits; or (vi) pursue any other remedy available in law or equity.

You may be able to offset the taxes losses on the new property.