I've got an amazing Chicago property tax attorney that I highly suggest using. 

Cost segregation study can be a great way to unlock tax savings, even for properties you’ve owned a while.

Welcome to property tax investing. 

If your rental "loses" $10K per year, sure that's tax deductible, but it's certainly not a tax credit.

Paying it off would save interest but remove that deduction and lock up cash you could use for another property with better after-tax returns.

That improves the block, raises tax revenue, reduces blight, and gives buyers move-in-ready options.If investors stopped buying distressed houses tomorrow, you’d see:• fewer renovated homes• more unsafe/dated properties sitting vacant• lower neighborhood appeal• and fewer entry-level houses anyone actually wantsThat doesn’t help affordability, it hurts it.The real driver of rising prices is supply versus demand, not whether an investor bought the house first.

These are the exact areas I dig into as well, because they quickly reveal whether someone can realistically meet the participation requirements that drive STR tax benefits.Understanding W-2 demands, average stay length, hands-on involvement, and the dynamics with a property manager tells you almost everything about how the STR will perform and how the tax strategy should be structured.Most investors underestimate how much these factors impact both their numbers and their ability to use the losses.

Units 1 & 2 rent for $1,550/month eachThe remaining single unit rents for $900/monthTotal current market rents should be at least 15% higher given the location and conditionLight renovations can boost rents by 25-30%, creating immediate income increasesAdditional Revenue Streams: The 400 sq/ft rooftop deck and garden outdoor space offer potential for higher rent premiumsThe 400 sq/ft two-car garage can be leased separately or repurposed, which is a significant value-add in PhillyZoning and Expansion Potential:The property is zoned RM-1, with existing rights to build 2 additional units by right, without zoning board hearings or red tape.

That’s insane.Protest your taxes people.

If you’re working a normal full-time W-2 job, you generally can’t qualify as a Real Estate Professional under the tax rules.