This means researching the market, understanding tenant demand, and ensuring the cash flow comfortably covers the loan payments.

If you look at Orlando, 365 market for the most part but it is one of the toughest markets to succeed in.

This deal highlighted our ability to identify market-ready properties and move swiftly to generate a solid profit in a short time frame.

As a syndicator, I can say that raising capital has become much more challenging since 2022, so many deals have closed in the last two (2) years that aren't fully funded and that are continuing to raise capital after the closing.There's likely truth to the money being raised going towards reserves, which is a very important part of any syndication deal (running out of money is one of the big reasons why syndication deals don't go well). 

Is this common in the Chicago market or markets with high property tax? 

I was in a similar position without the rezone, I can put a third unit on my duplexes property, but after running buildout numbers it makes far more sense to use that capital towards just buying another duplex.

This is a real concern, especially in competitive markets.

My question is: how do I start with little personal capital?

Since you started renting the property on December 1, 2023, you can only deduct expenses like utilities, insurance, and repairs from that date onward.Any expenses before that date (like remodeling) are considered capital improvements and must be depreciated over time, not deducted immediately.

At what point does accepting capital, using the capital in private lending, and paying interest on the capital become a security?