I tend to think the economics in the South Bay are strong for this strategy but my thoughts on that may differ from yours..Due to high home costs our local market, investors struggle to maintain cash flow under standard lending conditions/structures. 

.: 624 Bathroom Information# of Baths (Total): 1# of Full Baths: 1 Bedroom Information# of Bedrooms: 3 Parking / Garage, Exterior Features, Taxes / AssessmentsParking / Garage InformationPrimary Garage Type: DetachedParking Type: GarageGarage Type: Detached# of Parking Spaces: 1 Exterior InformationRoof Type: AsphaltStructural Style: ColonialProperty Condition: FairPatio Type: Porch - No stepExterior Material: WoodConstruction Quality (1-Lowest, 10-Highest): 6Architectural Style: Colonial

Beyond that, I am intrigued by the possibility of building a portfolio of small multifamily properties and generating cash flow to increase my flexibility and time with my two young sons.  

The other part of wholesaling that is a possible red flag is Equity Stripping, AKA Illegal Flipping, this was heavily regulated till a few years ago by lenders, especially M.I. companies, they have relaxed the rules, but was a problem pre and post crash. seeing the increase in this activity seems eerily familiar,  like 2007 all over again. just be careful especially with your license, Disclose Early, Often, and in Writing, My license is too valuable to me to be involved in this type of transaction, so i steer clear. if my entity is on the contract, I am the one closing. period. 

Therefore, you can't sell the home to yourself to increase the tax basis.  

A quick mls search shows the cheapest apartment rented in Framingham that was listed in the last 6 months was rented for 925 and Ashland $975 so it looks like you have room to increase rents if your building is in decent shape.  

We've exchanged emails about terms and conditions and the application form he sent me was very questionable!

I think that's my fear that I'll get cut out of the deal unless I go through someone I trust like family...which means working on their timeline and under their conditions.

But to answer your questions 1) Either by wire transfer or cashiers check2) Maybe depends on your state3) The condition of the property, how much you can buy it for, what is the ARV, many more questions.4) YES

I would not have bought this to be a rental property, since the numbers don't make sense.The risk of renting it out is that the house condition continues to worsen faster than we can afford to fix it, or yet more problems are found.