I have a habit of being very reactionary in stressful situations so my hope is with more knowledge that I can condition myself to avoid overpaying.

Year end taxes was just a button click away.

How stressful is it to deal with low income tenants?

I spoke to my lawyer in regards to my options and i have 3 options:1) Keep the existing lease (exp Oct 2021)2) Provide a new 1 Yr Agreement3) Month to Month LeaseWhen i initially spoke to the tenant, the tenant was stressed out about signing a 1 yr lease, and i wanted to give him the benefit of the doubt (before i found out about the payment issue). 

But the Fall/ Winter months are incredible, and as long as you pay the $400-600 a year for Flood Insurance, much of the stress is alleviated.  

Much of these considerations, by U.S. banks, are getting their spread sheets & accounts books looking in better order, as they face the the FED is now asking banks to be able to pass stress tests, in case any financial crisis, like occurred in 2008-2009, might flare up in late 2020 or in 2021.

I'm a grad student with little money and experience, but tons of drive!

Because they can just hit that button I think that they do not read the ad and just ask the same question for every rental they see.   

This may sound simplistic, but I stopped stressing about all the little fees a long time ago.

Firstly, you should realize that you do have control of the situation, you just need to let the tenant know that ASAP.We all know that moving can be stressful, but it does not release an adult from their responsibility to comply to the lease terms they agreed upon.