It seems in order of increasing profitability:LTR < MTR < STRGiven that I'm based in the Denver metro area, unless I'm occupying the property as my primary residence, STR is out the question, as Denver has cracked down on the short tern rental laws.

If I buy a property for short term rental and do a cost segregation study to speed up depreciation, can I later decide to convert to a primary residence?

I have tried going through the conventional route of HELOC and Home Equity Loan for my primary residence.

Since you already have the cash, you can avoid that added cost.Lower Risk: By purchasing outright, you're minimizing your risk and giving yourself time to learn the process without the pressure of loan payments and short-term financing deadlines.Better Refinancing Terms: After you purchase and stabilize the property, you can refinance it with a traditional lender at a lower rate and pull cash out for your next investment.This approach keeps things simple and allows you to focus on learning without the complications of high-interest debt.Let me know if you need more advice!

For example, suppose your primary residence, rental properties, and employment are all in the same area.

There's always the traditional sub-metering option if you are going in and doing some extensive work to the property as well but I've found that to be prohibitively expensive on my properties so far. 

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For example, I had a client who converted a student property in a college town to a traditional rental, but the key was that the asset wasn’t performing well.

Let’s discuss the hidden costs and potential pitfalls of traditional financing methods that many investors overlook.

I currently own a duplex and a sfh (my primary resi) on the south side of Chicago.