I would suggest obtaining insurance and naming the Mortgagee as loss payee and sending that in to see if they will remove their insurance since your policy has them insured.  

I removed personal info and info that identifies the actual property and people involved.

I want an air tight transaction and will have an attorney review and give me their seal of approval once I feel like I have thought of every possible negative outcome for myself.So far the possible negatives I have been able to think of are below and my intended solution will follow:Dodd FrankFinding a tenant without a license (I would like to market to those who have high days on market)facing penalty for performing broker transactions without a licenseI would market, find motivated seller, let them know that I can provide them with a cash offer, they can sell with a realtor (pay the commissions, spruce up costs, holding costs, etc.) or they can sell on lease option and get someone better than a regular tenant in the home.I would use standard docs specific to my state but they would be modified to include the below:Letter of IntentI would have them sign an intent to sell where in it, it would state that the property will be purchased via an option and the option will be in the name of a land trust.it will state that I as an owner and friend will be allowed to assist in the finding of a tenant, negotiate the lease terms, and be allowed to show the property without any compensation and at my own expense.LeaseMy lease will have verbiage stating that the tenant will be responsible for repairs, and normal up keep / wear and tear associated with the property up to $250 (this is my benefit I sell to the seller so that they don't have to deal with every tiny little tenant issue.Tenant will be responsible for all utilities and they are to be in the tenants namewill be allowed to extend twice, each for a period of 12 monthsTenant needs to inform owner of extension no less than 30 days before lease expirationthere will be no mention of the option within the lease, PITI will still be owners responsibilityWaiver of Liability associated with LeaseI will have a document created stating that the owner is solely responsible for the final approval, screening and placement of a tenant and that there will not be any recourse for myselfOptionFor the consideration of $1 (with receipt from trust to the owner) the trust will have the option to purchase the property no later than 45 days after the expiration of the lease.The purchase price will be agreed upon within 5 business days before or after the date of the lease expiration and if both parties are unable to agree upon a price, the owner and trust will each get their own licensed appraiser, average the two out and split the costs.this will be an option / right of first refusal hybrid and will very clearly lay out the expectations that there will not be any seller financing, the transaction will be in all cash or if the beneficiary of the trust so decides to get a loan from a reputable / licensed lending institution they need to provide a pre qual letter within 14 calendar days of the lease expiration and mutually agree upon a closing date.I would then sell my beneficiary rights to the trust for $5k, and exit the transaction.

It's my understanding that the wind/hail portion of damage is already covered under regular insurance policies with a much higher deductible, I believe, like 10%, so you'd be paying that first $20K yourself, anyway.

If you are using a servicer, you may want to find your actual yield by using an adjusted monthly payment which removes the monthly servicing charge, i.e., the net payment to you.

Hello BP,I've been far removed from the real estate industry for a while now.  

I regularly wish I was closer to that market - if I were you I would look down in the crossroads area or those little neighborhoods north of the plaza (can't remember the name). 

[editing post to remove contact info]

Already it takes an amazing amount of time off my regular work to plan, research and manage, but it's worked well so far and I've come to believe we can pull it off :-)

When I remove this from the denominator, my COC increases by 2%-3% which is quit significant!