Save the awkward moment later, and don't hide it now.

It will be awkward if it goes out in those scenarios.  

Not to say I wouldn't considering representing, but I don't think theres a large enough clientele out there that values a socially awkward realtor showing up in a multicolored Accord, ripping cabinets down and chasing roaches around with an air nailer.

Regardless of what happened its going to be an awkward conversation for the tenant to go through, and he will likely get defensive. 

But it's still awkward to start the conversation. 

I am in a awkward position, since I have my license with him.  

I didn't end up buying that one for unrelated reasons but.....AWKWARD!

Nothing says curb appeal more than what used to be the garage door window, now awkwardly framed by cheap siding!

I'm relatively new so having someone in my corner to do those potentially awkward negotiations seems beneficial.

IMO there is no need to create a potential conflict with a lease clause (because it's worded awkwardly for example) and the Federal law.