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.  

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

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

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.

@J Shoe I will start by saying consult with a personal attorney and CPA (and have them work together.)Typically people buy in an LLC just to keep their name off the record and for asset protection and operation agreements.As a sole investor a lot of people will buy in their personal name so they can more easily obtain quality financing, and then move the asset into the LLC.A lot of people of California use trusts (DSTs) to hold the asset, so they are not contributing to the problem of over taxation in CA, as CA has a franchise filing fee of $800 every year for each LLC.Just some things to think about, but find the professionals that can tailor a system for you personally.Cheers

It's important to take all things into consideration especially when dealing with taxation, favorable landlord rights, demand for properties and economic growth.Here's a great article:YouWhy is Florida residential rental units a good investment? 

I want to avoid the taxation of converting any of these investments into cash to invest.