And I told him I wouldn't put him here if I didn't believe in him, and I was going to do everything in my power to deliver him the most opportunity and hands-on support to make this transition a success. 

As long as you can pay down your credit card debt with your normal income you can keep everything in your real estate business in a separate account that you can then use to buy more real estate.You should consider picking up everything in the package as well even if they don't necessarily cash flow well. 1031 exchanges can be a powerful wealth building tool that can see you into more multifamily properties faster.

Besides  being the "Next Portland" or a better version of itself, Pittsburgh has really been dubbed as the 2nd "Silicon Valley" with it's tech influence largely funded by big named companies such as Google, Apple, Facebook, Autodesk, Uber and Ford AI Initiative among others who have set up shop here.

In addition, you can limit your liability exposure as well as take the burden of credit lines off your personal income/assets as well as family's borrowing power since an LLC., C-Corp, LLP are all their own self standing entities.  

He proceeded to tell me that if 4 investors invested in a property that they bought for 1.8 million (College Housing) is chump change to what they could do with a Chick Fil A. I

Full disclosure, this house is a flip.During the showing we noticed there was a little water in the basement, but the sump pump wasn't running as the power had been shut off on the first floor. 

You certainly don't need his product, but he made powerful arguments about the many problems they had with Arbitrage. 

I'm unlikely to convince my wife to allow me to invest more than $250k -- if I leveraged that assuming 25% down, then I have the potential buying power of $1M. 

Yes.A couple things worth noting:1. if your purchase agreement contains a section of representations and warranties from the seller such as a) i own the property; b) it is free and clear; c) there are no outstanding judgments/liens; etc., and anything later turns out to be untrue, you could pursue the seller for breach.2.

I have been guilty of staying cheap in areas that were cheap...never buy properties in bad area is the best lesson...I had  camera installed and saw thief cut the main power line and steal the cameras in Joliet and police reports and police is waste of time and insurance can be expensive...I have had simplisafe wireless alarm system that is great for identifying who comes in and leaves..because you can assign codes to each worker.if you could have a combo system of simplisafe  or another wireless system with a camera system combo that captures who is going in and out might be your best option...you need alarm system with video capture because we still have people leaving garbage in parking lot that alarms can't prevent...I have not come across anything better that has active alarm system with videos.