My strategy (which I have used extensively, see my bio) gives each property time to build up some equity, but still allows for the lowest down payments available in the marketplace, and the lowest interest rates.  

Use every opportunity you have to make sure you have a solid contractor and then build up a relationship.Today, we have hundreds of homes and while both I and other staff build relationships with contractors we obviously don't meet them onsite at jobs very often. 

If you have more properties with smaller cash flow for each one, you may be able to build up a larger net worth over time because you're leveraging your money more and you have more properties to appreciate.

Being that my main focus is building a portfolio I feel instead I should just pay an extra $100 on principal as it will be beneficial, and then save as much as I can to build up my savings.Is there a certain percentage to pay extra on principal each month that would be the sweet spot to get the best of both worlds?

Over time you can build up a portfolio of single families in Dupage or Will; but your cash flow numbers won't be as good.

Looks like if we were to build up the berm higher (or some kind of retaining wall) and over a certain distance to where the property elevates we could avoid this in the future. 

@Eric Lee Nation    I did ins claims in another life for 14 years - I do not recommend that EVER as someone's employment but I did learn a few things.Here's 2 things agents or no one will tell you -- your Replacement value (RV) on the house is JUICED up way higher than what's realistic -- however you have a relatively inexpensive house so it's not much of an issue - but typically the reason they juice the RV is to get your wind/hail deductible higher -- typically 1%, 2%, 3%, 5% of RV is what your wind/hail deductible will be even if you had a $1k or whatever other deductible they offer for any other peril -- so follow me for a minute - you bought a rental for $150k -- they've juiced the replacement cost to $250k the most likely loss in KS or the midwest in general is going to be wind/hail --- the math actuarial nerds do this so the casino or the ins company in this case has the upper hand -- do the math what a 2% or 3% deductible on a $250k house will be -- I have a commercial building insd for over a million -- the lowest wind/hail ded they will give me is 5% -- the only reason I have ins at this point is I'm required to -- the wind hail coverage is worthless to me with as high as the deductible is.Anyways with that out of the way - ask your agent if you have a 3% option - at that RCV cost they figured of $99k that wouldnt be much different than the $2500 all perils coverage you have now -- Also I'd wager as someone mentioned dropping the med payments to others coverage -- it probably wont make a bit of difference in your policy cost -- I could be wrong - but I'd guess $25-50 dollars a year -- your coverage is the price it is due to the perceived wind/hail risk the company is putting on KS.I'm with Big Red and have been for a # of years -- your price to insure that house is on par with what I get from them for that replacement cost -- though i think State Farms game is a bit different they really jack up the Replacement cost so I have higher wind/hail deductibles -- I'd make out good if the house burnt down or a tornado destroyed it - but for a hail claim there wouldnt be much there.

Important thing is to have a heat shield/reflector in the attic of your house to help prevent heat build up in the attic.

I don’t have enough experience with Corporations to know if the same holds true for them and business loans or if you would have to build up business credit first.

If those disclaimers were never obtained you’ll likely need fresh ink from all of the heirs to fix this.