Most occupied property insurance policies will cover "vandalism and malicious mischief" but there are different forms of policies so you'll have to ask.

You should reach out to @Melissa Haworth she can get the actual numbers/rents on STRs in the area to help run your comps.Each building is different, each area is different, it is important to find accurate data to make good decisions.

@Jesse Simmons I want to tackle this from a little different perspective if you don't mind.  

There are also a lot of different options in real estate to single family residential, multifamily, commercial, NNN and then being on the debt side of being the lender which has cash flow but not appreciation. 

So, when investing in areas they don’t really know, investors should research the different property Class submarkets.

That's looking at it through a narrow lens though, when you zoom out to 5-10-15 years down the road and calculate the difference, in my experience the appreciation has been far more beneficial than the $200 difference per month in cash flow from a different market.

Best advice to you would be to use that VA loan as many times as you can and buy primary residences for a year, rent them out and then buy something else with the VA!

I ended up buying a different property two blocks away.  

Indeed as Stevo mentioned, there are no Canadian versions but it still works, the only difference is the mortgage interest rate is compounded monthly in the USA vs semi-annually in Canada but that doesn't make a huge difference in payments.

Since there are technically 2 cities called Kansas City and they are located in different states (with different laws and building codes), it's very important to distinguish between the two, local referred to as KCMO and KCK.So, a long way to ask, are you interested in real estate in KCMO or KCK to start?