Normally commercial buildings are rented with triple net (NNN) leases and the rent rate is by the square foot.

I have to answer your question in a slightly different way, as in the case of Triple Net leases different rules apply.The best financing (CTL financing) is available if you have an Investment Grade Tenant such as Walgreens and a remaining lease term of at least 10 years plus.CTL financing is negotiable at 100% plus, but you need to know the "language" and the rules of the game.There is no school where you can learn the game, and the insiders typically do not share their knowledge.So CTL financing is determined by the creditworthiness of the tenant and the strength of the lease; not by the appraised value of the building.With Non-Investment grade tenants you (only) have access to regular sources of financing, and the normal rules apply.Hope this helps.Louis Bergman

He wants to sell the building for $275,000 he currently gets $2800 for rent and it's a triple net lease (the bar pays the insurance and taxes of about $400/month).

I.e if you are in a place with long, cold winters and where the norm is to construct {residential} properties with full basements, then an uninsulated, yet conditioned, basement could be the source of 20+% of your heat loss.Dustin - a 3.5" air gap may be reasonable in Kansas (if you wall assembly was air tight ... even then I am doubtful) - however, it does nothing about the 12 - 15% of your wall that is framing and a thermal bridge.When it comes to windows, there are advantages to triple glazing and inert gases (though they do eventually normalize with the atmosphere) ... however a well-built double glazed window with an insulated frame will match, or out perform a triple glazed window with your run-of-the-mill aluminium or vinyl frame.   

Heck she could have paid triple the value. 

Passing through triple net on top of the $22.

For instance, if your brother is being paid 55/hr his billable rate is double if not triple.

The risk  seems low at first glance as the triple net side of the building is a dentist office owned by a corporate dental company with 7 years remaining and two 10 year options.

An agent replied saying that they would triple the coverage to $1 million and it would be a minimal increase in price.

Those who are already wealthy and want to preserve what they already have in a safer way are happy to double to triple outpace inflation annually they just do not want lots of their capital at risk.This is very different from a much younger and opportunistic investor still trying to create wealth and taking higher risk strategies.