Then, the DAY BEFORE closing day, the lender informs her that the condo is in fact 'non warrantable' and they can't lend on a traditional conventional loan and need to change the loan terms to a 'non warrantable' loan product which greatly increases her interest rate.

A cash our refinance only makes sense if you've increased your equity after you bought.In terms of the DTI issue, you can overcome this by obtaining commercial loans like DSCR and hard money financing, rather than conventional.

They also increased my line of credit by another $40k due to extra equity within the property that I can now use to acquire more units.

YES it's that simple,Good luck 

In my opinion, flipping is hands on and there is little a book will teach you on flipping a house(especially if you never acquired a property before).The only way to learn is to go through the experience.Start off with a simple project - a property with minimal work that needs to be done(replacing a roof, HVAC, Painting, Flooring).Don't buy anything with water damage, fire damage, foundation, bathroom remodel or a kitchen remodel.Move on to more complicated projects after you have a couple of successful flips.

I self manage and for me, adding another here locally does not increase workload much.  

If the property has recently been renovated I would definitely buy occupied because it reduces your risk and increases your cash flow right out of the gate.

Imo, what you would spend on the deductible would increase your basis in the property.

Increased property taxes may have an effect on your total investment returns and cash flow.Make Connections with Local Investors: Gaining knowledge of the Chicago market may be achieved by establishing connections with real estate brokers, property managers, and other experts in the field.

Seek out locations that are undergoing gentrification, development, or expansion where property prices may increase over time.Creative Financing: To fund your local deals, consider unique financing solutions including partnerships, seller financing, or private loans.