We added value to this property by investing $20,000 in key renovations, focusing on improving curb appeal, modernizing the interiors, and ensuring the home met market demands.

Without knowing how many bedrooms & bathrooms, who your target guest is and what your strategy is (rent-by-room, entire place, etc) it's impossible to answer.

However, the FHA buyers were by far the worse in the Chicago market.

Any deprecation expense/recapture for/by the seller prior to the sale is no longer relevant.As far as loin points, not sure these are amortized at all for tax purposes.

I’d just raise rent by $5 per month lol 

For him, this equated to $100 / hour working as a self-managing landlord and increased his ROI by 10%I'll say that again, it increased his ROI by 10%Good Luck :)

BACKGROUND: Bought a property SUBJECT 2 an existing 1st lien (lets say serviced by Shellpoint) years ago.

If the seller has already discounted the property considerably to justify the work needed, then you have to take that into consideration.If the seller is trying to sell the property full price needing repairs that’s a whole different story.Roof or foundation.No, I offered $5K below asking after they slashed the price by 20K 

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When you factor in the tax deduction you get on the mortgage interest, this 5% rate on a CD closes matches what you would save on interest by paying down the mortgage.