All tenants are paying substantially less than market (average is ~750).

Whatever you do, don't go the Vito Corleone horse-head route! 

I have a big picture in my head i want to build up a million dollar company.

I’m scratching my head….Do I:1) Call him and say, “Hey, I see you requested an application for another property that I own…”2) Send him the application and say nothing and let him figure out it’s me?

Now if new owner doesn't renew, their head is on chopping block for not continuing to have permit in place but are renting it out. 

The thought popped into my head last night and wondered if it was even a thing. 

You might even feel like you're banging your head against the wall trying to find anything.

It's never good to screw over one investor to get a head yourself, I am/was very tempted to call him out by name on here so others would know to be cautious but I will take the high ground.

Thanks to any info  or replays to this post a head of time! 

Though, even through house hacking, not having any capital cushioning me in the event I have a room(s) go vacant for too long makes me extremely uncomfortable, and I'd rather just wait until I'm able to invest without so much risk rather than getting in over my head and setting myself back with even MORE debt.