@John OksI recommend finding an accountant specializing in real estate taxation.

It looks like the regulation will go the way of permitting and hotel-style taxation

Professionally, I have study and working experience in the German Taxation Laws and know that Taxation is a crucial and vital aspect in any business in any country.I already have property here in Germany and currently planning to expand to Dubai and Miami USA. 

Called out on it by IRS and NY State Dept of Taxation, provided my documentation and cited the code to both entities, which resulted in avoiding tax court and a reversal of tax liabilities.  

Jay,I recommend finding an accountant who specializes in real estate taxation over one that is local. 

Every GP, real estate investor, makes mistakes, doesn't time the market perfectly etc, looking for the perfect is the enemy of the good. good REITs right now, take a look at ADC - agree realty, does multi-tenant triple net large shopping centers and has better growth outlook than Realty income-O-, 6% vrs 4%, which is also great company, both stand to benefit from low supply of retail space, last 5-10 yrs construction-wise, and thus better rents going forward, and interest rates should fall near term, lowering Cap rates and increasing underlying asset values and sales proceeds (only hold REITS in a tax-sheltered account, 401k or IRA, due to high taxation of the dividends-ordinary income) Good Luck

I can't say I fully understand, but I certainly get the main point:  Transferring the asset out of the S-corp will be a (capital) gain triggering event.I think (because I don't remember exactly) that in 2017 I changed the election of the corp from C to S in order avoid double taxation in the case of selling the property. 

For more details refer to the link above.No, you can not invest your retirement funds into the LLC that you personally own (with or without a partner), this would be considered prohibited transaction per IRS:https://www.irs.gov/retirement-plans/plan-participant-employee/retirement-topics-prohibited-transactions Regardless if you use an IRA or 401k - all investments you make with your retirement funds must be passive in order to avoid taxation. 

However, liability issues came up about a Canadian owning US property outside of an LLC , but also the heavy taxation of an LLC for a Canadian.

The way I look at it, the main differences being risk and taxation.