This does not look like the environment where you can do a classic "buy, fix, rent, refinance" . 

- Classical.

Low end properties are a classic newbie trap, especially for remote investors. 

Put the deal making to the side for a while and read some of the classics, like Napoleon Hill's 'Grow Rich with Peace of Mind.'

I will share my "Most Expensive Lesson" in the comments.To kick things off, here are ten examples of expensive lessons or mistakes in real estate investing:Underestimated Repairs: The classic pitfall where the cost of repairs and renovations far exceeds initial estimates, impacting the overall budget and profitability.Tax Liens: Failing to account for or being unaware of existing tax liens on a property can result in unexpected financial burdens.Contractor Liens: Not settling payments or disputes with contractors can lead to liens against your property, complicating sales or refinancing.HOA Fines: Overlooking or violating Homeowners Association (HOA) rules can lead to significant fines and headaches.Bad Loan Products: Opting for loan products without fully understanding their terms can lead to unfavorable financial conditions, such as higher interest rates or unfavorable repayment terms.Ignoring Zoning Laws: Investing in a property without a clear understanding of local zoning laws may restrict its use, affecting your investment strategy.Overpaying for a Property: Lack of research or getting caught in a bidding war can result in paying much more than the property's worth.Neglecting Due Diligence: Skipping thorough inspections and background checks can uncover unpleasant surprises after the purchase is finalized.Poor Tenant Screening: Failing to properly screen tenants can lead to unpaid rent, property damage, and costly evictions.Underestimating Market Risk: Not considering market fluctuations can lead to investments that don't pay off as expected, especially in volatile or declining markets.We've all been there in one way or another, facing setbacks that seemed daunting at the time.

Here’s an overview of the deal 👇// 16 year owner // 100% classic units// 33 units in Indianapolis// Avg rent was $400 below marketThe letter cost $1.

This is a classic case of stepping over dollars to save pennies.

Classic CPA answer 😛 but it is in fact true.

However you do have the opportunity to look at a 1031 exchange which would indefinitely defer all of the tax on that $240K gain.Selling one larger property to use the proceeds to purchase several smaller properties is a classic 1031 strategy called a diversification exchange. 

Matt, If you are looking at historically built properties such as your classic bungalows, 2-flat and 3-flats in Chicago, many of those properties were built well before the modern zoning code was established.