In my experience, allowing these professionals to guide you can be highly beneficial, as they are likely to recommend properties they would be comfortable managing.

I've been studying for a while and see investing as a cycle, times of high activity (chasing the deal) and times of latency (allowing the deal to mature).

Real estate often rewards patience, and holding in a market like this can allow you to build wealth steadily as property values grow.

-Creates a solid foundation for passive income, allowing you to reinvest future cash flow into other opportunities without as much financial risk.Cons:-Ties up a large amount of capital that could potentially be used to generate higher returns elsewhere (like another STR or other investments).

After spending 25 years as a Software Engineering and Product leader, I’m now exploring the world of real estate investing (REI) and looking forward to learning from all of you.My goal is to leverage my current investments and savings to build a real estate portfolio that will eventually allow me to transition away from my current career.

In Chicago you request a CHA Burden sheet and that gross number minus utility allowance will be what you get in addition to making sure bedroom size is adequate.  

Negative $700/month doesn't put a dent into our household free cash flow and that allows us to buy properties that appreciate rather than cash flow. 

In any contract you don't typically need a clause saying what you CAN do, its assumed you can do anything legally allowed as an owner including sell.

Many insurance companies do not allow adding a landlord as additional insured.  

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.