A friend of mine once said "When you are an Energy Analyst / Building Automation Programmer, all of your problems look like a nail." 

The Mortgagee has the ability to accept or reject insurance in most cases through the language in the security instrument.  

BP had been incredibly instrumental in helping me decide what I want to do as far as real estate.

At the risk of not looking like a professional seller, you could explain the situation to the buyer and get a payoff statement from the senior mortgage with updated payment info from the automated line. 

Effective Date: 10-06-1980 5313.09 Instrument of cancellation of land contract.A judgment for the vendor shall operate to cancel the land installment contract as of a date to be specified by the court.

Once you have sold the property the owner carry becomes a debt instrument and is not eligible for a 1031 exchange on it's own.However there is a way to still combine the owner carry note with a 1031 exchange.  

I'm REALLY open to suggestions on how to follow-up with hangups in an automated way.

Let's clean up this terminology.A Mortgagee is on title since they are granted, through the security instrument (mortgage, deed of trust) an interest in the real property.  

What are the best services out there to automate these processes?  

But if your property has a high-end kitchen and the other one doesn't, an appraiser might add $10k back and value yours at $110k.You might try to get your hands on a few appraisals to learn how appraisers value a property and add/subtract value based on features, square footage, and fixtures/finish.While I'm sure this varies wildly, I've found that some realtors rely too heavily on automated comps or CMAs when valuing properties, and these can be off by a wide margin.