I'd contact a tax expert in both countries rather than rely on a travel website for complex tax issues.

Terry and Caney,
The figures posted by Terry are more in line with what I expected. I think you also got a great deal in regard to "My lawyer in Toronto charged me $100.00 for translating and notarizing my RCMP police record report, my birth certificate, and correlated copies of my passport." - The translating part alone on that I would've thought would have cost more than $100.00.
I actually have a notary stamp. (Not that I can notarize my own documents) But in any event in stuff aside from that which needs to be done by the consulate any notarizing I could have done with no cost.
I vaguely recall reading about the multiple property situation in which wife takes the smaller house. It's a good idea but in practice you end tieing up quite a bit of money that can otherwise be invested. As an active investment I'm not sure the returns on a casa particular are particularly good. (Granted I realize you can do a restaurant / bar whatever as well) If your falsely declaring the money being paid to you by tourists like most casa particulars then the returns could be decent. But frankly if I'm doing business ever in Cuba it's going to be 100% above board. I believe the tax rate hits 50% pretty quickly in Cuba. An active investment that is only generating perhaps 15% return isn't particularly appealing. Might as well buy a business at 3-5x earnings in North America. With that you get an actually liquid business atleast and some level of protection / guarantees.
Maybe I'm wrong in my understanding of the casa particular business. But I figured on a per room basis these places make around $300 / month in Holguin over a 12 month period. Some maybe a bit more, others less. If you get 4 rooms you are looking at $1,200 a month gross. But I think like half that ends up going out in taxes. You are also probably going to spend atleast 50ish thousand to get a 4 bedroom, 4 bathroom rental if not 5 bedroom, 5 bathroom given you probably don't want to not be present in the risk that clients break rules. That tells me I'd be looking at maybe $7,200 a year on a $50,000 investment if not more where I also have to probably be present a significant amount of the time or atleast pay someone to be present. I also run risks related to being decommissioned and need to pay for ongoing upkeep. The numbers might be better in a place where per room rental rates are high. (Say for example if you had a villa with a pool in a popular district of Havana) At the standard $20 a night (or less if bargained for) rate that most of the islands casa particulars charge outside of Havana I don't really see much opportunity in it.
The recent seizures of the hot spots in Havana only further my caution in terms of starting any type of significant business. (Bolabana, Starbien, El Litoral) amongst others. Since going to Holguin it seems the private bars open for a bit then seem to close out of nowhere. It certainly isn't because these guys aren't making any money if you see the amount of people at them. Starbien was the most shocking of those to be closed due to who the owner was.
I'm more in the wait and see what happens going forward mindset at the moment. If policies on private businesses change in the future then I'll be more active.
Not sure why I couldn't edit my previous post.
YanquiBoy. Will be on that. I go at the end of the month to see my accountant. Hes good and well versed. If he doesn't know I'll look elsewhere for a tax expert. I anticipate he will be knowledgeable.

You can't own 2 properties in Cuba unless one is a 'city' property and the other deemed as a vacation property.
Income earned in Cuba, tax would be a killer. It's a sliding scale, between 10-50%. First 3000cup is tax free. The next 3000 is 10%, the next 3000 is 15% and so on, till you hit 50%.
I don't plan on setting up any business other than maybe growing and selling some tomatoes...lol
As mentioned, previously... I am not aware, not that i know everybody...lol, that has lost their house because of a divorce, in Cuba. This is not Canada or....... This is, especially, true, if you are not married. Losing property or assets in your home country is not going to happen. A non issue, imo.
You will pay, if married, alimony, but it's the equivalent of going out on a night out, once a month, so immaterial. It's actually less than that. Used to be about 50cup/month but my wife says they raised it a few years ago. Might be double that, now. Don't know. There is no means test.
I had a good friend in Havana, now deceased. A former minister. You could set your calendar by how often he changed wives. Every 10 years. Never lost his house in Miramar. One of his sons now has title. Also a good friend of mine, now in Florida with his family. He's selling the house in Miramar.

Just a note about something said here. A house can be registered in the name of a minor child. However, the house cannot be sold until the child reaches the age of majority (18).

Thank you,
Thats interesting news for me. I'll have to consider that option. Although theres a reasonable chance prior to my daughter turning 18 I'd buy something with a much higher price tag. It is a good way to protect my investment at the very least.

I sound like a broken record. If you have PR, the only way you can have property rights, you will not lose the property if you split up.
Maybe, you should talk to a Cuban lawyer.

Understood but it will be in my daughter's name. The chances of my relationship souring with my daughter are much less than with her mother naturally speaking. Its much less likely my daughter says daddy you can't be here get out then my fiancee.
With that said 18 years is a bit of an obscene to be locked into a property. Especially if we have more kids and decide a bigger property is needed etc.
gres, I have an Italiano/Cubano friend in Cam city with PR status... he WAS previously married to a cubana, but has now since divorced her. He's also very good friends with a lot of Ministry officials there in the city of Camagüey... and they've schooled him on how to protect his assets in the same way that they regularly do. What he's been told is that anything that a single man owns in Cuba BEFORE he gets married, those personal possessions of his will always remain his exclusive property AFTER getting married... but with one important exception. Prior to the 10th year anniversary, the wife is only entitled to half of anything that was purchased DURING the marriage. After 10 years of marriage, Cuban law dictates that EVERYTHING owned both before and after becoming married is to then be split 50/50 upon divorce.
This is why so many Cuban men owning strong financial assets and entering into a marriage will keep their Cuban wives for just short of 10 years before divorcing them. They then do 1 of 2 things afterwards... they either remarry their Cuban wife to set the clock again, or they trade her in completely for a brand new much younger model... which is by far more common. Of course before entering into their next new marriage, they first acquire more new assets in advance so that those will be totally protected too... well, for at least 10 years.
Knowing all of that upfront couldn't possibly have helped my Italiano/Cubano friend to avoid his financial loss upon divorce... he basically had to give his casa particular to his ex-wife as settlement in the divorce... with him keeping ownership of the farm in the campo that they had also acquired as husband and wife together... both properties purchased AFTER they became married, and after he was able to secure his PR status with the help of the marriage certificate. He has since sold the farm and has used that money to buy a new casa and completely renovated it to be his new casa particular and home. He's still single at the moment, but he's now in a position to remarry again, and the next time he does... his new wife will not be entitled to any of his new current assets for at least 10 years. But of course we all know what will come first for her later. Will he remarry her after the divorce? I doubt it. Just like his aging amigos cubanos working in the Ministry offices, he also likes the new younger models too much.
Terry