It's not that complicated or worth paying someone several thousand dollars.Love the name STR Secrets as well.

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..

I get the general gist of it but also know it’s a little more complicated than the videos make it out to be.

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

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.