I produce reports roughly every two weeks.

I don't even know areas where you could spend that much and even get an incredible amount of appreciation to make up for it.

He has a stable W-2 job producing 100k/year and an additional savings of 50k.

I have seen properties in my market that have tried this: basically using a GRM of their Airbnb revenue to justify an incredibly inflated price.  

(Again, Utah's housing market.)TL;DR: If you have a good relationship and both are willing to take hits and roll with the punches without getting offended and hating on each other, it can work out and the profits and gains can be incredibly good.

That's an incredibly bad sign.Sorry to rain on your parade, Thomas, but this doesn't smell right.

Ray Kroc's and the McDonald's story is incredible! 

Depending on how much cash flow the propertues produce, we may flip more houses to save up for additional properties as well until we can live off the cash flow. 

You are considering that for the Long Term, the Millenials are not going to be able to have the JOB's that produce enough Income in order to Buy SFH's.

There are a lot of off-market deal opportunities which may produce better results than using zillow, realtor, MLS, etc.Be aware that with an FHA loan you will be paying mortgage insurance throughout the entire span of the loan, unlike other loans where the mortgage insurance stops after a certain percentage of the principal has been paid off.Prepare yourself with some financial homework on the properties you are looking at and how much ROI you are going to get and be ready to pull the trigger.Also be very aware that Massachusetts is a tenant friendly state with almost seemingly unfair laws 'against' landlords so it is best to be aware of the Massachusetts Tenant and Landlord Laws and have a very good tenant screening process.