The 'threat' of the specific performance clause in reality is used to get the seller a better cash settlement than they would get without it as opposed to actually getting a court order for the specific performance. 

Exterior of these homes is fine (skirting is one and they all have decks).

Since this will be the start of our real estate investing journey (opposed to our current residence) we wanted to know if we should look into a regular homeowners/flood insurance policy or an umbrella policy since we'll be acquiring additional rentals in the near future?

You should probably prohibit the flying of any flags on the exterior of the property.  

Can anyone recommend a good Commercial friendly broker that I may consider working under; I would like to stay on the investing side, however I am not opposed to working on the Realtor side of things in the Commercial world as I have taken a really strong interest in that area of real estate.

I am not opposed to getting 70% out and leaving 30 in.

I would also try to look at it from every angle on the exterior to understand the potential damage. 

shower curtain (or none at all to highlight the nice tile), heavy duty floor/exterior paint for the garage floor. 

I liked the fact that their efforts were supported by a place on Home Depot's referral system, as opposed to my leaving messages on someone's phone, not knowing if I'll ever hear back...

Mostly you will find lead based paint on the window sills and exterior.