This also helps me to forecast seasonality on my properties.

But that's me.To answer your question, I'm not in the business of recycling dirty money but I think it's pretty well known and established the the proceeds for criminality and the drug trade is invested in all sort of business, especially real estate.

The 1031 exchange is designed to give you a loophole: You are not considered to be selling and buying, you are simply trading your property for a different one or ones.

If i was starting from scratch, i'd probably start by developing a job skill, probably in the trades like electrician or plumber.

At $377K/door, this building's costs will be nearly 2X what a similar building would trade for in this location.  

What do you use for skip trading and how accurate is it?

If I knew that I wouldn't be here, I'd day-trade on that information (stock ticker $MBB, for example, it's an ETF, so it functions as a stock, you can short it, or buy puts, etc) and be a billionaire well prior to Q1 2025!

My thought is is use the Rent Ready feature of reporting his payment history to the credit bureau so it can work in his favor as a trade line, but I'm wondering if this is an unnecessary added step since he can already pull transactions on his bank side. 

I would NEVER trade that experience for anything, despite the hassles. 

You mentioned a career change, I think going into the trades like plumbing and electrical are great and you can make good money doing those, but I think you may be taking on too much by trying to do that right now.