I'm of the same opinion on this (own rentals in Fort Bend and Central TX).

Before considering this, I do not want to set up the precedent that I will just bend whenever people ask for handouts. but I also want to be fair and am looking for unbiased advice on how to respond to this request.

it should offend him, and so be it.As @joe said this property with a long history of neglect, water intrusion has done far more than bend some rafters.  

You need to get in the game"I see people are bending the 'rules' of the game to make the current real estate market make sense.

Just from a manual inspection with my agent, I estimate 20k at least in repairs, that in my opinion are not ticky-tacky (gutters/water management is broken, Not enough support poles in the basement holding up the house, poor installation of a front porch that is putting pressure on the internal brick foundation that is starting to bend in).My gut feeling is that the seller will be opposed to reducing the price based on conversations with my agent and the seller's agent.

Although I bought lots in Hood river and Bend Oregon from my bank for 20 cents on the dollar in 2010 2011..  

Hi Bigger Pockets Investors,My wife and I purchased a rental property in Bend, Oregon 1.5 years ago for $480k and put another 30k into rehabbing it.

An investment here is almost as bad as a time share when you factor "ALL" the fees and monthly expenses they bend you over for.

So we will eventually sell and part ways with Colorado (where we live now).I've scoured the following markets: Reno, NV, Salt Lake City, the Oregon coast, Bend, OR, Sacramento, CA, Lake Tahoe (CA/NV) and touched on most places in between.

Bloomington, West Lafayette and South Bend are all major college cities that can work with the right strategy.