I'm curious about this. i have most of my rentals in Maryland (Baltimore County) and evictions are not extremely complicated AFAIK,I don't want to hijack this thread with a lot of bellyaching so I'll DM you the story if you care to hear it.

Quote from @Hector Espinosa: Hi,I'm negotiating a seller financing deal which may be my first one and would like to ask for some advise about and what are advantages and disadvantages about seller financing deals.These are the seller financing terms:House Price: $330,000.00 USD​ (Sellers still owe ~$301,000 USD)Down Payment: 5% = $16,500 USD​Loan Amount: $313, 500​ (Monthly payments will be amortized as a 30 years loan​)Interest Rate: 4.531%Balloon Loan Term: 5 YearsMonthly Payment (P&I): $1,594.24​Closing Costs:  ~$3300 ​Zip Code: 74105Observations:       * HVAC requires an update but pending to inspection (replacing with a new one will cost ~$10,000 - $15,000 USD )     * Expected Rent Income: $2,000- $2,300 but this is has been really complicated to get a good estimate because is all over the place in the different sites I have checked

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

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

Trying to get an owner occ loan was a chore ended up getting it done but what a pain.. owner occ underwriters are used to very simple tax returns and when you have more complicated ones it just takes longer..

They are rules of thumb we use to function day to day because the FACTS are too needlessly complicated to use to make every decision in life.

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?

@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.