How comfortable are you devoting time to researching tax code and methodology to prepare a cost segregation?

I'm concerned that if I bring up the matter of withholding security deposit to cover the costs , they might cause more damage to the house prior to vacating this month. 

Today, let's discuss property tax assessments.

Remember that the IRS has strict rules regarding SDIRAs, and any violation of these rules could result in penalties and adverse tax consequences.

In most jurisdictions that are primarily democrat elected judges they will extend the sale date so long as no prior extensions have been granted.

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This means you are doing it strictly for the cash flow.If it were me, I would go the ADU route, Rents could be comparable to the condo without the HOA dues (yes higher Cap-Ex but those are long term expenses), and with everything on one property, things are just easier to manage (one mortgage, one property tax bill, one insurance, etc.). 

Another thing to check when running your numbers is the POTENTIAL taxes on the property.

They carry forward but would be much stronger from a tax planning perspective if they were used to offset active income. 

I recently received the PT-100 personal property tax return for filing.