Turnkey property, so assuming 5k in improvements, 4k in closing costs.

I do not know about Chicago's landlord and tenant laws but something isn't right if 7 months later the tenant is still there and hasn't paid anything.I would do an autopsy on my lease, how you started the eviction process and if it was completed correctly, how you handled the tenants first late payment, did the PM company screen the tenant per your instructions or could your tenant screening process be improved??

I now oversee the day-to-day operations for our MEP, insulation/air sealing and renewable energy crews (which is actually only one crew right now; we're planning to expand to 2 - 3 crews this year).

If you enjoyed engineering and didn't have sucky bosses, and you put that same energy and passion into that and saved the absolute max in your 401k, you'd have gone very far and not had to worry about money for long.

@Steven Hamilton II - given the nature of lead abatement, it could be considered an improvement rather than a repair, and as such the net expenditure would be depreciable rather than deductible.

My main concern is how can we achieve our goal in a timely manner while being the most tax efficient?

A face lift, improvements, updating exterior, any of that needed?

One of the properties is a 1 Br/1Ba that needs some improvement, there may be a moisture problem, it has a noticeable bug problem, last year there was a plumbing problem, yea...it needs some work.I am not sure about the classifications nor the current living environment of the other property, but my guess is it's 50/50 on similarity.The owner is offering my friend both properties for $150k with $5k down.

I buy at a discount because of the depressed value of the asset and then I know I can improve the performance of the asset and increase its value.

Maybe keep your reasonings why vague...say it's for "home improvement", and when they offer secured against your home, just say "no thanks".The 0% check offers that credit cards send out are not expensive.