Hopefully his students are better, I don’t like the idea of thousands of people entering the industry trying to find sellers willing to sell via subto who all think it’s okay to bend the truth, especially with transactions like subto that are complicated and require a lot of trust on behalf of the seller (that the buyer will do what they say and keep making the payments and not wreck the seller’s credit potentially affecting their ability to have a place to live in the future because you can’t even rent an apartment with bad credit). 

Save for some unusual complications, you seemingly met all the conditions for your tax benefits.Now, to traps and gotchas.Trap 1.

(In the simple / non complicated scenario)- time ranges - in the best / simple case scenario how long should I expect this process to take? 

@Shaheen Ahmed you can find all the info you need online if you know where to look - except that the City of Detroit Assessor's Office is consistently undervaluing properties to keep property taxes attractive for investors - to keep improving the city:)Here's some copy & paste infor for Michigan Property Taxes that you might be able to use as a template for other areas - or you could start investing in Detroit:)----------------------------------------------------------------------------------------------------Michigan has some of the most complicated property taxes in the USA.

That’s a good plan. 1031 is a bit complicated but you can continue to roll cost segregation benefits forward  

Cross border taxation is very complicated, most developed countries like the US and Canada have sophisticated systems to ensure their residents pay taxes, and you are not likely to be able to achieve your goal of not paying Canadian taxes on Florida income while a Canadian resident. 

Is there a reason that you need such a complicated structure?

The concept isn't that complicated and the first one lays it out pretty well. 

A purchase agreement is a waste of time and energy and complicates the issue for Harry Homeowner.This is not a beginner strategy as there are federal laws concerning approaching debtors who have been given a notice of foreclosure.

The loans were varied and some were able to close sooner than others and they wanted to close before the others but we held out because we needed to close all of them at the same time to avoid any last minute standoffs or complications.