It probably because I have weathered the storms of bad investments, bad investment decisions, poor timing, stock market crashes, lack of experience, government taxation/regulation/corruption.

Avoid taxation.

Multiple LLC's have also some expense and certainly hassle associated with them. in Oregon we're charged annually and then there is more complexity with accounting plus annual taxation costs.

Also you need to setup the right entity in order to avoid double taxation etc.  

However, they aren't a magic bullet solution to avoid taxation and there are plenty of rules to abide by - the IRS isn't keen on just giving out loans after all.

Property tax at 1.25% (slightly conservative) for ~$800/month. 

I'm curious about taxation, legal issues etc.

As previously mentioned though, there is the foreign tax credit route you could use to avoid double taxation.

You don't want to hold real estate in S-corp and C-corp - Owning Rentals in an S Corporation Might Be a Costly Mistake.That leaves you with the LLC - and even here there are many things to be discussed (when to do it, how to do it, proper transfer to preserve title insurance chain, DOS, financing, management, distribution of properties per entity, insurance etc.).The LLC is a legal concept, of no particular taxation benefit (you can have it as a disregarded entity for taxation, or taxed as a S-corp or C-corp).

., consult an accountant versed in cross boarder taxation before embarking in an LLC as they are typically not recognized by the CRA.