You asked about a property you have listed for sale and property taxes that are coming due and the consequences of not paying them until the property sells.Generally, the local taxing authority will impose an interest penalty on any unpaid balance after the due date with a long grace period before you would have to worry about unpaid property taxes affecting your ownership of the property or your ability to sell.In all likelihood, the property taxes will become a part of the closing and will be deducted from your proceeds at the time of sale.By the way, property taxes are always in first lien position ahead of any other debts like mortgages.

It's almost $1000/yr with 2% deductible ($4k) with $200k value.

My biggest concern is to deal with the eviction if they wouldn't move out, but hope the double rent deduction from the remaining balance in escrow will avoid such scenario. 

The income they use is a 2 year average and you cannot write off a ton of deductions.

Tax Strategy: We are keen on implementing a tax strategy that allows us to maximize our deductions and reinvest in the business.

I don’t think I qualify for the 121 exclusion since it’s been house hacked and I actually made 75% of the house a rental property and filed taxes using deductions and depreciation.  

@Levi SiegelVery limited info, so can't be all that much help here. 

In my financial statement to the tenant concerning the deposit I itemized all the deductions. 

@Atul Mohlajee not sure who your attorney is, but three of our attorneys approved our automatically renewing lease that requires tenant to give proper Notice so it does NOT auto-renewal.Michigan law also allows any length of Notice requirement, ours is 60 days.That aside, a judge can rule however they want, forcing the losing side to go through an expensive appeal process.Regarding the 1.5 SD, they are legally allowed to deduct any damages, then apply the rest to outstanding rent.My opinion is that the PMC should only be able to charge:1) Rent + lease utilities until a replacement tenant is found (Michigan statute)2) Whatever the lease contract states

I literally wrote a check for the deductible.