IRS / other tax municipal liens and special tax assessments are notoriously "sticky" and usually trump all others, even 1st mortgages. 

Trump has a good reason to have an anonymous LLC head a company he owns, I doubt that you do. 

But even a savvy businessman like Donald Trump couldn't keep his casinos open there(I thought the house never loses? 

For example, a unit in something like the Trump Tower or the Ritz Carlton would be a luxurious place to live, but that may not be appropriate for you if your goal is income versus just having a nice place to stay from time to time.         

Generally federal law trumps what's written in private contracts.

Especially ones that focus on real estate.Probably the most common way people show breakeven or losses is as Chris said is with depreciation.The super nice strategy in recent years is the Trump Tax Act of 2017.   

Posts like this are so.. to paraphrase Donald Trump, I don't want to use "idiotic" because that would be insulting.

Perhaps if Trump is elected President but I digress. 

I would like to build my own real estate system, a bit like what Trump did (on a much smaller scale) in which a company can run properly without it's owner.So that's the goal, and to achieve that goal I need at the minimum a real estate agent, a bookkeeper, a CPA, an attorney, a property manager and either a handyman or contracted maintenance help.

It now looks to me like a with-holding tax from Canada might actually trump capital gains in either country for this situation, and might end up being about 25% of the value.