By combining you get savings, a single occureance deductible that @Mike H. references, ability to have multiple titled properties (personal and llc) on 1 policy, 1 bill, etc.

What I am saying is he can lock in a permanent tax waiver by selling now AND have a large enough amount of capital that allows him to go buy a different type of RE that will significantly boost his cash flow NOW (think 4-10x) and give him the ability to force a large amount of appreciation in the next 2 yrs vs 20 yrs AND not have to worry about the market taking that appreciation away from him if he buys in the right area and manages it well.

I found people to be much more happy with it being an individual lease and not having to worry about their roommates ability to pay rent.

Obviously the CPA in the States would know better my plan is to sit down with a Charter Accountant in Canada and also have a booking with Tom Wheelwrights Business " Wealth Ability on the 10th of May about this exact thing before i pull the trigger on anything.

Why should the pay me a commission for the ability to list when they can list for significantly less? 

Signing contracts to purchase without intent or ability to close is called FRAUD.

I get about 400 5 star reviews per year and I am a super host with @Avery Carl  Any more than 5 and I’d have two choices: start outsourcing or lose my ability to scale.

The relevant date is the sale/exchange date, not the date a property becomes your primary residence or the date a bill becomes law.  

This is not an indictment on you as a broker, your skills or abilities but purely a factor of the product type.

Some laptops such as the Surface Pro have the ability for the screen to disconnect and serve as a tablet.