of condos / apartments / townhouses listed within a relatively small area on the North Side (River North up to Lakeview) which makes me nervous about the potential for oversupply within that market. 

Anything falling within that description would be self-dealing and result in severe tax penalties for the IRA.A self-directed IRA allows the IRA to diversify beyond the stock market into assets such as real estate and private lending, but everything is done through the IRA and exclusively for the benefit of the IRA. 

I would NOT want to create an environment where people looking for a quick buck become a headache around the neighborhood and consequently relating back to me.2.

If you sell it, you would get some money now but loose out on the long term rental benefits. 

I am relatively new at this.

You can write off the investment related interest even if it is funded by the Heloc.But if you will take standard deduction, it doesn’t matter.If your itemized deduction were greater than standard deduction (24k if married in 2018), you could deduct the interest you paid on the heloc to the extent of your net investment income. 

I'm a big fan of the benefits of home staging.

Qualifying for the VA Loan is relatively easy 0 down etc.

NOW, as a buyer, I can understand how helpful it is for me to have the TDS before I pay to have any inspections completed, because anything on the TDS related, for example, to a past roof leak could be looked at during roof inspection, or related to a past fungal/dry rot issue could be looked at by pest inspection to ensure the past repairs held through time.

I'm probably a little higher on the equity side than most, but I figure if I have good equity, my debt service is probably relatively low compared to rental rates and will also help ride out the soft patches.