If there aren't many people interested in the property, a wholesaler would have to consider an offer that has an inspection contingency otherwise they risk holding the property longer than they anticipated.However, if you're in a hot market (and who isn't these days), you may be competing with people who are willing to go after the property so aggressively that they drop all contingencies; this would represent less risk to the wholesaler of the buyer backing out so naturally they would likely choose this offer over yours with contingencies.If you're finding that all deals you're coming across do not allow contingencies, it may be valuable to spend some time learning how to expertly predict repair costs on your own so you can determine if a deal is a good one without paying for inspections before getting it under contract. 

It will help with liability, makes the unit more attractive with natural light, and will make your property more desirable when you sell. 

Finally, any advice on what I should include in the policy to make sure I'm fully covered in regards to manmade and natural disasters?

They have a combined 45 years of experience with rehabs, new construction, and commercial in Chicago so I have naturally learned a lot from them over the years and tend to trust their judgment.My questions - Is 25% down overkill?

No doubt, it's a risk tho..Naturally I would much prefer something with less overhead that performs well, and I'm willing to buy my way into an established market, but then I'm starting from scratch, and frankly despite having some reasonable tools at my discretion I don't really know how to data mine the entire US.Now that the dust is starting to settle after years of being in the trenches with this duplex, it's clear to really make money with this you have to have a portfolio, as I read in an article from this site, 1 or 2 rentals ain't gonna do it.

They usually want you to put some skin in the game, so you might have to put down 10-30% down payment, depending on the deal and your experience.

And naturally, contractors hate that.

Otherwise, I just have a natural conversation with them and learn more about them. 

Suggest you go the electric route--less or  no maintenance costs, and when repair is needed, inexpensive compared to most gas fired boilers or furnaces.I would also have a small natural gas wall space heater installed somewhere on the main living floor (not in bedrooms) just in case of power outage and / or for supplemental heating.  

What is the nature of the LLC?