Sadly this was yesterday's news: http://www.boston.com/news/local/massachusetts/201...Same street, just sayin'...

Any recommendation on what I should be looking for, asking for documents etc..., other than updates and repairs on the property.

B. (1) BUYER HAS: 30 Days After Acceptance, unless otherwise agreed in writing, to: (i) complete all Buyer Investigations; review all disclosures, reports, lease documents to be assumed by Buyer pursuant to paragraph 8B(5), and other applicable information, which Buyer receives from Seller; and approve all matters affecting the Property; and (ii) Deliver to Seller Signed Copies of Statutory and Lead Disclosures and other disclosures Delivered by Seller in accordance with paragraph 10A. (2) Within the time specified in paragraph 14B(1), Buyer may request that Seller make repairs or take any other action regarding the Property (C.A.R.

Make sure you have all the documents like copy of his contractors license and the contract.

Proper borrower documentation.  

Even though the returns are lower than I am use to, I could sign some documents, pay closing cost and start cash flowing +/-$2000 a month (not including maintenance cost).

Itemize all repairs needed ( get real proposals) include $15/hour for your time for whatever you do yourself, then subtract from SD, supply past tnenant with documentation of those costs and return balance if any. 

@Katey TataWelcome.You may not want to make this complicated.If you draft an Agreement to Purchase a property, draft another to sell that Agreement and sit with a Real Estate Attorney from Massachusetts to review the documents, you should be ready to "Just Do It!"

As the expert, it probably falls to you to break the news to them.If what they really need is an income stream, you should definitely make them an offer involving seller financing.

If the borrower uses rental income to qualify or if the loan amount is greater than $417,000, six (6) months of reserves must be documented.