We have been working to be extremely conservative with our estimates but with this being our first go at this, any additional expertise is greatly appreciated! 

What I noticed so far is extremely high property taxes. 

Selling would likely mean taking on new loans at much higher rates, reducing your cash flow margin unless the new properties are stellar performers.Transaction Costs and Taxes: Selling could trigger capital gains taxes (depending on exemptions) and other selling costs, eating into your net proceeds.

Verifying last 2 years of rental history and income extremely important to find the “best of the worst”.Make sure you understand the Class of properties you are looking at and the corresponding results to expect.The City of Detroit has 183 Neighborhoods we’ve analyzed.PM us if you’d like to discuss this logical approach in greater detail!

This is an example of private lending which is different than the IRA owning real estate and does not trigger UDFI/UBIT tax.

We're exploring creative ways to provide him with the cash needed for the down payment while avoiding triggering a taxable event.One strategy we're considering is purchasing his future primary residence ourselves, making the mortgage payments, and then, once we've built enough equity—comparable to the appraised value of his rental properties—transferring the title to him as a form of exchange.What are your thoughts on this approach?

Another example of this is Newark, extremely strict laws making land lording a second job.When finding the right area to invest, towns with more lenient land lording laws and proximity to public transportation tend to be a receipt for success.  

Just make sure you guys are comfortable with the area before pulling the trigger.

In the “old” days, people would have the seller pay the lender so as to not “alert” the lender that a property sale had taken place, so that the lender def wouldn’t trigger the so called “due on sale” that’s a part of almost every mortgage or deed of trust document.  

It is in an extremely desirable area in Watertown, CT.