My mortgage is 2,000 including insurance, taxes.

I found a good deal that I can move on, and would like to approach the home owner prior to the auction and possibly make them some money as well.I Found the owner, the tax information, searched the property, done comps(well working them now) and in a few days I'll do a complete Title History and Chain of Title and if necessary buy Title Insurance.

That includes (but not limited to) Mortgage payments, Taxes, Insurance, Utilities, HOA fees, etc. that occur during the Rehab phase and up until the property is fully rented.3. 

Adding in guesses for annual tax/insurance at 5k a piece and a 4% interest rate, the total monthly payment comes to around $2,450. 

I work pretty closely with an insurance group now, but I would still be happy to connect to see how we can benefit each other down the road!

That is a question for a contractor to actually look at the chimney and see what condition it is in and whether the house is stable enough for it to be removed.

As an extreme example to prove my point, lets say you borrow $1 million on a property producing $10,000 in monthly gross rent with the following terms:conventional  residential- 4.5% for 30 years: monthly payment = $5067commercial 6.5% for 15 years: monthly payment = $8,711Keep in mind, this property, even in a modestly expensive state has taxes of 10% and insurance at 5%.

Once you factor in taxes of $475/mo and insurance at $115/mo, your total monthly payments will be $1610 and that's before the other expenses that you mentioned.

I am looking for recommendations for an insurance agent in the Independence, Mo. area that is familiar with buy and hold investing.  

I believe there is an online registry of sink hole homes, at least those with insurance claims.