Based on my experience managing thousands of properties over the past 20 years, chances are against you; it's unlikely that you will have to file a claim or that the claim will be so small that you won't need your insurance. 

Hi Olufunke,It seems like you are based in Texas? 

Connect with @Stuart Udis a wealth of knowledge and based in Philly 

The investors I work with here are mostly looking at student rentals near the university or focusing on areas near Fort Jackson, so there is always a good rental base here!

The 1031 is not a bad idea again it would yield 2-3 properties based on down payment and closing costs.

So, if you plan on using it as your primary residence you may be able to "inherit" the low property tax base value, but if/when you stop using it as your primary residence, it can be reassessed to current market value.

We now have them come semi annually to do routine maintenance so we can get the 25+ years out of it4.) both octopus furnaces we have replaced were both wrapped in asbestos so replacing them was best for the safety of the propertyI would also suggest when talking to HVAC reps to ask if they are commission based or not, that’s a good indicator as well if you have the means to be a self fixer that’s great but not sure it’s always the best and easiest approach 

Plus garage, and fully renovatedMy question is should I be looking at this purely based on cost/sq ft, or should I give a percentage value to the property it sits on, then assign a percentage value to the structure itself to figure out the fair market value?

These properties don't really have negative cash flow, except when evaluating based on the asking price.

Organic rent growth should typically match inflation.