Simmer gently for 6 months (seasoning time in lender speak) 5. 

Just some gentle feedback.  

Turn it into artist lofts, do some sound proofing and maybe band practice rooms, people looking for storage for collections, small office space for massage therapists, etc.Easy long term rentals, especially if you are under local rates.

Also, this lease will have been added to time and time again over the years and massaged to best fit the local courts and rulings.Don't risk issues with your several hundred thousand dollar asset with a .02 cent lease. 

I need the occasional gentle nudge to keep me going down this road of real estate investing.

Besides that, our tenants are usually only in the property for 3-4 hours a day, they almost never use appliances, and are very gentle on floors, cabinets, etc.

In my situation, I gently probed for their "future plans" before non-renewing just to see where their head was at. 

I'm pretty new to the investing game, so be gentle after reading this. i must be poorer than i thought, if someone offered me $500 to drive 20 miles (not all day) i would do it in a heartbeat. sounds like your agent either doesn't really want to represent you or maybe not investors in general. if he had much experience working with investors i would've hoped he would have told you upfront about his issues with small commissions.

I have learned who to say yes to and who to gently steer away.

There is a gentle slope upward to the road but major flooding may cover up to the road.