Talk to some good agents in your area who have success selling condos quickly and see if the proposition looks different when your done.  

My proposition is, if one was able to bet against the spread so to speak by choosing the correct properties in the correct geography, you would able to beat the average RE market performance.

Would this be considered a risky proposition for an investor?

@Kerry Baird - Thanks, I understand owner-occupied properties are a lower risk proposition for lenders, and thus rates are lower.

Historical PricesSource: https://www.financialsamurai.com/are-you-a-real-mi...We had the dot-com bubble in the late 90's, followed by the housing crisis (collapse) of 2008, and in my opinion the dollar is the next bubble, see Forbes article below:https://www.forbes.com/sites/kenrapoza/2015/01/26/...Additionally, if you do agree that there is a much higher inflation rate than the Fed reports, stashing cash and earning interest below 8% is a LOSING proposition.

Based on the price and rents it sounds like somewhere in central ma but not Worcester or maybe on the south coast.Anyhow, converting the 2nd parlor to an extra bedroom is a risky proposition.

Let them know what you're doing and have your value proposition in hand.

I'm just curious what everyone thinks a good proposition would be for a deal like this, he wants to make it work just looking for a starting point that helps both parties.

We're missing part of the story.Sorry for the tough love but lenders are in the business to make money and lending to borrowers with bad credit is a losing proposition for all parties...the lender, the borrower, and the general public.

However, I think that I have a unique value proposition in that I'm providing the services of a real estate attorney and broker/Realtor at no added cost.