He's kicking and screaming and by responding, even if only to counter his points, you are engaging this behavior.  

As the listing agent, I personally would not advise a client to negotiate reduced rent with a tenant who is metaphorically screaming at me that he/she is in financial distress, especially with such a large rent amount at stake.

A little unrelated but, I once dated a girl that cursed and screamed at drivers when she was the one doing the bad driving.

A 20-something seeking FHA financing for an investment property just screams risk and red tape.But don't take my word for it.  

I had to involve the police when first floor ran screaming at me in my car on a public street, yanked open my passenger car door while I was in it, and entered the car screaming at me aggressively while I was calling 911, (all because we had made every effort to avoid a confrontation with her), but the police only went to warn her, did not arrest her.  

One way to do this is to threaten to cut everything, and then back off based on who screams the loudest. 

Portland is a great place I worked up there for years and it would seem you would have a great op for maybe a air bnb or even a room rental property depending on the location and the ability for college studentsI'm in a pickle myself I bought a rehab property and completely gutted it with all new everythingjust need the money to completegot it rented for a screaming deal-650 a month and I'm paying all utilities at leat its kind of making the paymentkeep your options open and look in the area if you can for ops on getting the rents you needif you do a lease option make sure you get a nice amount down with good terms for you that way in 6 months when they default you get the cash you need to cover expenses until you get it filled againGood luck!

All of those factors scream to me that you should not do this deal, structure, financing, or strategy starting out.

wow you just captured lazy landlord concept in a very serious no nonsense refuse to laugh at myself way.Yes that is exactly what the lazy landlord series is about Learning how to tackle the big doableJobs that seem daunting Doing these jobs safely and to a high standard of craftsmanship The lazy part is that many of us procrastinate and really do not want to tackle these jobs This series is for those who may be on the fence or are about to embark on a similar renovAtion It's a place to share tips and tricks And read as I go through one of these renovStions I will share whatever I gleaned from the processSo Deanna I am not calling you lazyI'm calling myself lazy because I have the ability to do and I usually end up dragging myself kicking and screaming to the job site

. $16k in operating expenses without a mortgage seems like you would be cutting it real close if you financed, and none of those areas scream appreciation to me.