What system(s) are being utilized to manage these opportunities? 

If you can negotiate the right combination of property price, term of option, and consideration payment you will give the seller, you now have the luxury to utilize the 'time' you have bought with the option to find the highest and best use for the property.So why give up a non-refundable consideration to the seller, when there are those that simply negotiate a $500 or so refundable deposit on a straight purchase and sale agreement? 

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However, I do not much about renters/owners agreement on paying utilities...

How do I estimate the cost of Utilities?

The office manager requested I file an extension because I cannot see a CPA until after tax season. 

And my friend has extensive logger data for her system in New Hampshire. 

I've been leaning that direction purely because I have a small HELOC as part of a loan too so by selling I can utilize the 50K difference toward a multi-family dwelling instead.

The strategy would work  better if it were your primary residence, but it becomes more difficult if you're trying to convert a SFH to a true two-tenant duplex.1) You'd must likely be violating zoning (Unless area was zoned MF), so you'd have to hope the conversion flies under the radar.2) Utilities is the biggest hurdle, as a SFH only has one water, electric, and gas meter.

That being said, $3750 is the new qualifying income, minus $1250 for rent, minus $200 for utilities, minus $150 for Phones and TV, minus $1000 for two expensive vehicles.