You’ll also be able to get out of it quicker, if/when it comes to that, being directly immersed into your market versus trying to find and understand valuation and risk factors remotely.

As an attorney, I would not respond via a thread because the question would require me or any attorney to review the lease and compare versus the requirements of Chicago's Ordinance. 

Is it more in the appearance versus what is actually said?

It may make more sense to go online versus the traditional route and vice versa.

If you don’t have a lender go to multiple lenders and even if you do have a lender, talk with other lenders as well and have them show you what would happen if you were to refinance versus staying on the FHA loan.

Question: Why, in your situation, would you HELOC versus Refi? 

I want to follow up and try to figure out the material versus labor components because it's more than I was expecting."

Versus learning to be a landlord on a multi-unit rentals with higher cost and more moving parts.

What would be considered a good versus bad buy?

The advantage of buying this way versus a self directed IRA is that you can avoid all the self directed IRA shortcomings such as You cant directly fix up the place or do any improvements yourselfYou or any relative can’t stay in the place (if it’s a vacation rental, it’s nice to stay there plus it lets you know the quirks/updates that could use your attention that you’d never have realized unless you spent the time there)Also if it appreciates say 300k to 600k, to extract the property out of the IRA you must pay tax on the new appreciated price.Am I missing anything here?