Personally never heard of this scheme or way to set up transactions. 

I've brokered $75 million in DSCR and over 315 transactions.

Though fee schedules vary by company, generally speaking, you'll pay more up front for checkbook control and less over time, since the full custodial companies will have transaction fees not to mention the red tape of going through the custodian for all transactions. 

I've dabbled in hard money for a few years on both sides of the transaction and here are the 3 types of people in the business.

If you would like to get more than the cash you paid for the property and use the new appraised value, the shortest period I've seen is 3 months of waiting period between when you closed on your last loan or transaction to when you close on your next loan / transaction.More on DSCR loans in case helpful: DSCR loans won't use your income to underwrite the loan.

Based on research it appears Zelle is the only option that does not have a transaction fee for landlords.I did not include maintenance as a category since this can be done easily in a spreadsheet, but all of the options actually had pretty good maintenance and expense tracking.For Tax Support, all of the tools met the minimum for being able to export the financial information. 

A 1031 Exchange is a real estate transaction that takes advantage of a Federal tax law, so the state you do it in is of no consequence.

Hourly rates can range from $150 to $500 per hour, depending on the lawyer’s experience and the complexity of the documents.In New Jersey/Delaware Valley, the rates can be on the higher end due to the higher cost of legal services in these areas, with some attorneys charging upwards of $300 to $500 per hour.In areas with a lower cost of living, such as rural locations or states with a lower overall legal rate, the costs can be lower.It’s best to shop around and get quotes from a few attorneys familiar with private lending and real estate transactions.

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. 

(Think of it as you are the "bank" in a typical REO transaction).