Tell them to bring their camera, tape measure, mother in law and whatever else they need to make a decision but its too much to ask of the current tenant for a prospect to have multiple showings of an occupied place. 

Or, does the appraiser's field measure trump the county website?  

Some banks may go more conservative to 75% to reduce their own risk however its important to know this distinction because it could be the difference between getting the loan and not especially with people who have tight DTI ratios.My second point about the above is the "self sufficiency," rule that every is mentioning is not measured by taking 85% of gross rents to meet the entire PITIA of the property if its done in the actual underwriting guidelines you take the entire gross rents of all units and compare it to the PITIA of the property if the total monthly gross rents are the same or greater then it meets the self sufficiency tests for 3-4 unit properties.Regarding the income being above being more than the PITIA or monthly total obligation, this wouldnt happen anyway atleast on owner occupied properties because income on rental property is underwritten separately and added to income while liabilities are added as an obligation you have to qualify for.

I'm curious as to the psychology involved with external security measures. 

Once you find the property corners, try to get a good measurement between the corners and see if they are very close to what is on the plat.

If it’s important to you, your time investment per loan will likely be measured in a handful of hours; like much less than 10.

You should be able to find some type of meter that would measure at least the electricity being fed to the "accessory structure", which would take away any questions of who is using what.

And 36 Other Key Financial Measures" http://amzn.to/Zv0Zph (on Amazon) to understand how to measure and analyze the financial performance and returns of an income producing property.

Mostly to test the market since this is a new area, but I am willing to rent it out.I have had more interest than expected from the rental marketing, and I have 1 person very serious about renting it.I threw the property up at a higher rent then I would normally ask, again testing the market and not overly concerned if I actually rented it.So now my realtor called me back saying there is a very strong offer coming in buy a buyer, and I have a very serious renter interested.Here are the cash flow detailsIf I sell the property, I will net $17.5k on a sale price of $102k with me paying $3k towards their closing cost.If I rent the property @ $950 I will have a monthly cash flow of $380, and I will leave $5k of my own money in the deal when I get the property mortgaged (I have no mtg at this time)So this got me thinking, what kind of metrics can we use to measure if a property is better to buy and hold vs. flip ?

Go slow always take measurements to make sure your straight and squareAlso get some quality knee pads and enjoy!