Hey @Thomas Sheehan - you can't outsource investment decisions to other folks, you have to first figure out what a "good" investment is for you. 

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

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

You want an accountant who can help you strategize and who is responsive when you want to know the consequences of the financial decisions you are making throughout the year.Good luck.

Most of the time when I would analyze properties on the market the numbers just didn’t make sense, but when we found a property that worked we were able to move decisively. 

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. 

You have to have a coach that helps you deal with the decisions and priorities.

I’m excited about the potential of this property but want to make a well-informed decision.

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.

That being said, the trade off are higher fees and rates.