If I have the choice of paying $50k to the IRS or paying $10k more for the replacement deal, the choice is pretty easy. 

If the property qualifies as a separate activity, you may be eligible to claim bonus depreciation through a cost segregation study, which can provide substantial upfront deductions — particularly beneficial if you are in a higher tax bracket.However, if your income level is lower, the cost of the study may outweigh the benefit.

Perfect example of how BP can be so beneficial.

That waste is where the most beneficial lessons are learned.

Fix those steps or whatever else is needed.My personal choice is to own everything in an "Illinois Land Trust".

Its observed repeatedly in these forums but it's almost always too late to offer beneficial advice since the services have already been rendered.

Quote from @Christopher Rubio: Hey everyone,I’ve been diving deeper into rental strategies and keep coming across Section 8 (Housing Choice Voucher) investing.

If your return for investing in another property is greater than 8.5%, than it would be beneficial to invest rather than pay off the debt (would want a sufficient cushion above 8.5% to justify the added risk and work of investing in another property vs simply paying off debt). 

There is a lot to learn and being in the heat of it can be super beneficial.

Im wondering if I'd have better luck making more money off of multi family elsewhere.can anyone tell me what markets they'd recommend for house hacking/ multi family and if Chicago is still a good choice?