Hey @Erika Andersen I totally hear you in wanting to save some money and taking on the task yourself.

That means that you can buy a house on the South side -- identical to one on the North side and in its doppleganger (save race) neighborhood -- for literally a $100,000 less than you can on the North side.

Of course to maximize your tax benefit it needs to be sustainable over time. 

He likely needs to stay where he is, save up money for a downpayment on his own, and buy when HE is ready.He's not ready. 

That's 50k a year gone and you are losing tax write-offs and equity potential.

Be mindful of short-term capital gains tax, as profits from flips held for less than a year are taxed as ordinary income, and frequent flipping may result in self-employment taxes.While profits from flips do not qualify for 1031 exchanges (since flips are considered inventory, not investment properties), you can minimize your tax burden by deducting allowable expenses like renovation costs, loan interest, and holding expenses.If you're considering diversifying into rentals, explore opportunities to benefit from long-term tax advantages such as depreciation and lower long-term capital gains rates.

So we GAIN 7million + tax payors etc.. 

As more people placed more properties in STR inventory, and as more municipalities taxed and regulated the industry, the profitability of the overall industry has reverted to a much more aligned (lower) risk adjusted return.  

First, there are about 6 states that I refuse to invest in because of their tax laws and what I consider to be an unfriendly business environment.

We're fortunate to have an above-average income and live well below our means.This summer, we’ll be moving to Detroit (PCSing in August), and we’ve saved about $120,000 to invest in addition to having funds set aside for the home we’ll purchase in Detroit.The reason I’m posting is that I’m struggling to decide how to best allocate the $120k.