All of those questions can help your agent structure an offer that will be competitive against others. 

I find this level of underwriting lacking with many flippers as well, failing to properly consider the holding costs, insurance costs, taxes, etc.

I have managed to get a couple properties under contract, most of them fell through due to a lack of investor interest.

The areas I lack experience in would include construction, repairs and handyman work.  

Separately, there are tons of older extended stay hotels in all the major growth cities with people living in them paying (fairly high) monthly rates due to convenience or lack of qualification for typical rentals.

Before this, I’ve come across several older multi-family buildings that lack central AC (tenants use window units), don’t have in-unit washer/dryers, or have smaller square footage.Being from Boston, these issues wouldn’t normally be deal breakers for me, but my realtor mentioned that they might be for tenants in Columbus.

Thanks to all who messaged me privately and @Chris Mason, I found Auto Owners was pretty competitive.  

If you lack connections where you invest, having someone on the ground is valuable.

(a) If the Company establishes the title, or removes the alleged defect, lien orencumbrance, or cures the lack of a right of access to or from the land, or curesthe claim of unmarketability of title, or otherwise establishes the lien of the insuredmortgage, all as insured, in a reasonably diligent manner by any method, includinglitigation and the completion of any appeals therefrom, it shall have fully performedits obligations with respect to that matter and shall not be liable for any loss ordamage caused thereby.. . .To the extent that you are requesting compensation for the Alleged Damages, please see Condition8(a) of the Policy which provides the Company with the right to establish title as insured in areasonably diligent manner without being responsible for any loss or damage to the insured.

It is holding me back from proceeding because of lack of money to lock in contracts.