@Kevin,   Here is a big help of advice, I'm a Full time Insurance adjuster with a  large national carrier (well known), wholesale Investor and investor of 24 rentals.1st), I need to state this is 100% Fraud, I would NOT pay the claim if I was the one to get the case as an adjuster, as everyone knows we do carry a book of checks to write to homeowner on site.

You can also do some snooping on your own, like if there is a mortgage against the property, or how much a person of his age/previous income would get in SS, etc.If you find something concerning, you can either choose to have a more pointed finance conversation (which he will probably not take very well), or you can adjust your own finances to plan for his likely future dependence upon you.My old people are much younger than yours but between snooping the public records and general conversations we've determined that we will just plan for them to need us to step in and help financially a couple of decades from now.  

The Cash To Close is not supposed to be the same as your Closing Costs, two totally different calculations.Your closing costs, are well, your closing costs.Cash To Close, is purchase price, plus closing costs, (with proration adjustments) which gives a Total Costs.  

I am not sure yet of the expenses and have not adjusted for vacancies( I don't foresee any vacancy due to the fact that i have been here for the past 9 years and the restaurant has been here for 12).My question from the subject line is "how do I evaluate commercial property?"

Since I first posted this a while back, however, I've made some adjustments, some decisions, and have been marching forward and actually rockin' it! 

None of the leases have provisions for annual operating expense (ie CAM or NNN) adjustments, and my insurance and tax expenditures are increasing.  

If you can figure out the liens adjust your price accordingly and also reduce your offer to offset needed improvements.

This is money in the bank each year and if a recession hits i have almost no impact in my portfolio as i will just keep the building until the values adjust to my target sales price ($150k in this example). 

You need to decide what is more important to you....Enforcing your type A personality that demands rent on the first regardless of crcumstances because you are the landlord and they are the lowly tenant that should is blessed to live in your property and should always bow down before you OR think like a logical business man that recognizes the value in a long term tenant with a history of paying, albeit it late but for a logical reason and offer to make necessary adjustements that will benefit all parties.  

I used to be a licensed agent years ago, and when we sell a property, I still put owner/agent on the sign or in the online ad just to stop all the real estate agent calls trying to list my property.