On the other hand, I’m hesitant to simply pay down more of a property, as we don’t need the immediate cash flow.Fortunately, both my wife’s job and mine are recession-proof, which allows us to be a bit more aggressive with our investments.I’d really appreciate advice from investors who have experience with frequent moves or military service.

I have found that they worked really well when it comes to getting better tenants and better rents, and having less hassle, less headaches, and then getting a higher sales price; without paying closing costs or realtor fees.

Will it pay the full PITI plus Capex, management fees, maintenance etc?

Quote from @Paul Lucenti: Would you rather have monthly cash flow or would you prefer a quick pay day after 3-6 months?

Insurance would cover it, I would pay the deductible, and no assets would be lost.If you are in an area like San Diego where people are more likely to sue, a judge is more likely to find you guilty, and the payout is expected to be higher, you may consider an umbrella insurance policy.

However while people in Windsor doesn't have the luxury of high paying jobs that GTA residents have, is it just a temporary fever of buying houses, or there is really something going on in this city ? 

Make sure the tenants are paying market rent or above, otherwise your loan will be DSCR constrained.

Example: If a business buys an oven and it costs $5,000, and $1,000 for installation and setup, and $200 of delivery and transport fee. 

I ran some of your numbers, assumed rent of $1,290/unit and that you pay cash for the rehab costs.

They just pay the invoices.