My thought is that if I can get a property with some sort of cash flow, even if it's more work, I'll get both a cash flow going and a major education into landlording, then I can upgrade down to the line to a Class A or B.

I am new to real estate, and have been on an educational binge absorbing as much information as I can.

Getting the contractor is easy thanks to the nationwide database of contractors who can earn an accreditation after completing a 203k education/vetting process.

You'll find many novice investors have no clue, so work on your educational spiel.Then get real good at finding actual deals for investors.

As part of my education path before purchasing, I want to join a local real estate investment club.

One last thing, buy a couple of books on rentals and multifamily properties to educate your self. 

I cant speak for M1 or Roch Thomas, but I would do some more investigating before investing that much money in an education alone. 

Looking to further educate myself in real-estate investing and investing strategies

Getting out there is probably one of the best ways to educate yourself.

I measure the exterior of the house and make an educated guess on it.