Why does he want to save this house - sentimentality or some idea that it's going to explode in value?

Ok Bryan Tomko,I am going to give you the best advice I can to help you win this deal without overspending for it.First things first,you need to establish the exact condition of the property,the approximate after repair value,and the true current value of the property.You do this by having professional contractors do a full inspection of the property and estimate every possible repair and upgrades you need to get the property into full ARV condition.This is a 60 year old property in what I imagine is a harsh winter environment.Snow,ice,possible rodent and insect infestations,can and will deteriorate the property over time.I am going to assume a few things now.The roof probably hasn't been replaced in a long time,if ever,it will need replacing.The wiring probably needs repairs and/or replacement.The plumbing needs a inspection with a camera through every pipe to determine damage and replacement if needed.Especially the sewer pipes and main water lines bringing water to and sewage from the home to the city pipes.They are exposed more to the elements and can break over time.I'm guessing the kitchen and bathrooms have never been upgraded and replaced,they will need that completely.New drywall and repainting inside and out.All the costs of doing that work need to be put into your offer by deducting them from the after repair value which you will establish by getting comps from recently sold properties in that area.Once you have all that,you will now be able to sit down with your family and discuss this like a business transaction.No sentimental garbage,just business.You can hug it out with them when the contract is signed.You can use the fact that they are losing 700 per month in insurance as a reason to accept this deal immediately.Now make no mistake,they are going to be upset that the house isn't worth what they hoped it was at this moment.Don't argue with them!!!!

@Jacob White - I agree with your sentiment on Prop A.

I can second the sentiments on Haverhill by @Rob L., @Julie Manning, and @Tim Wilkinson.My fiancee and I just bought our first 3 fam in the Bradford area, and we have already decided that this is the place we plan to invest in the most. 

Looking back the bottom in terms of price seemed to be that ugly period of market sentiment where oil was less than $30 per barrel.  

We share sentiments.

I will provide commentary in bold to reflect my current sentiments or actual situation as it applies.Mission StatementIn an effort to get out of the rat race and become a B/I instead of an employee, I have decided to invest in real estate.

You said "I am NOT interested in wasting a bunch of people's time by marketing a bad deal to buyers" which is wonderful sentiment but trying to market and sell a property you don't own is a lot like going around selling the Brooklyn Bridge which you don't own.

And, to just chime in with the same sentiment, hand writing letters will get old VERY FAST.

s sentiment that 12% just to find a lender seems like a very high fee!