Other stuff you mentioned should be able to be mitigated but also should have been brought up what sounds like a lot sooner. 

Sooner or later, demand is going to significantly exceed supply In Calgary, and Calgary will be just as expensive as any other Canadian city.

Where can you make connections quicker, in order to start seeing deals sooner?

This is why it is important to enlist the services of an attorney sooner rather than later and have a reserve fund to cover all expenses until you are able to take possession of the property.

General rule of thumb is look for properties with Cleveland in the address, anything outside of that will have POS.Start looking for contractors sooner than later - they'll make or break the whole deal. 

Do you want to have your money tied up in an investment that's breaking even and waiting for appreciation/interest rates dropping, or put that money into a new investment that could generate cash sooner?

The purchase of the unit is going to be sooner a few months, you could wait to rehab both at the same time which could potentially help reduce the costs of the rehab. 

As most of you know, the National Association of Realtors set a date of August 17th, if not sooner (depending on the state) to be the day that ALL states change the way buyers work with agents (somewhat).

Any company insuring your properties without an inspection most likely has a clause buried deep in their policy allowing them to deny claims for conditions found on the property that do not meet their UW standards and they will deny you claim based on "the house should have not been insured with them anyway".Although the inspections can be annoying look at it from the other side.You pay them 1000 to 3000 a year to insure a rental property where they agree to pay out possibly hundreds of thousands of dollars if it burns down or up to 1 million if a tenant slips on a bananna peel and falls down the steps or the tenants dog bites someone and since you didn't enforce the tenant having their own renters policy to cover the dog bite the landlord's policy is paying out.The insurance company is very much like your rich uncle backing your business venture - you run the business, he takes on the financial risk from disasters, and doesn't even get a say in who lives in the property.Your rich uncle asking you to fix the steps, put up a handrail, etc which is in your and his best interest long term.Do you really want to rent out a property with a busted front step and a bad roof that is going to leak sooner than later?

On a "small" loan amount like his, he found it more beneficial to pay the extra .25% to rate to get the 3 year PPP. reason: it added only $17 per month to his payment every month; a small price to pay to open the door for refi or sale 2 years sooner.