I would highly recommend you create a Market Report in PriceLabs to see how similar properties nearby are actually performing.

Aren't you glad that some antisocial media influencer brought this "tax strategy" to your attention?

The math says to perform $500 sewer clearing each year instead of $5000 excavation, but the $5k bought peace of mind.

The contract must contain:the contractor’s name, address and telephone numberthe approximate start and completion date, including any contingencies that would change the completion datea description of the work to be performed and the materials to be provided to the consumer, including make; model number or any other identifying information; and the agreed-upon price for the work and materialsa notice advising you that you have three business days to cancel the contract, unless during an emergency you waive the right in writinga notice that all payments received by the contractor prior to completion of the contract work must be deposited in an escrow account

Has this property been working for a while with a track record of income performance?

Immediately, I performed a Roth conversion.

Tossed around quite a bit and it isn't what it once was, but the value is still very high based on past performance and brand recognition.

Ultimately it will depend on the property (banks perform stress test-debt ratio)-but I think 5 year term is what I found so far.

We've gotten that advice from an old timer in the trades, but Chicago is notoriously know for lagging with issuing permits and performing inspections.  

My wife and I have a few homes near campus we use as student rentals and they certainly perform well.