Older guy, body failing, construction worker(and a fire fighter, driver astronaut, walked Nixon's dog...Twice ect).

If you do bring up your concerns and they still fail to address them then it’s probably better to move on.

You failed to qualify, so the Experienced Realtor doesn't want your business. 

The city, highway district, developer and engineers and owners have all settled and the homes that were at risk have been removed along with the street that failed. 

A commercial loan technically should only be based on the income the property produces but at the same time they want to be sure you can cover it if it fails.

(risk versus reward, enough margin, etc)   "can this guy pull it off" (what is his experience, does he have other resources if he gets in trouble on his numbers), are his numbers right compared to other deals they have done) , and "If he can't, what am I stuck with if the HML is left holding the bag and the guy fails?  

“Fail to plan, plan to fail.” 

You are very likely to fail. 

Without expansion, the deal fails our analysis.Our analysis consists of a spreadsheet that was developed for cash flowing properties.

This happens frequently, often because of judgments/liens and/or the seller failed to understand that a prior loan modification did not forgive some of the balance but rather tacked it on the back end as a 2nd trust to be paid upon refinance/resale.