Did you lie to the mortgage co and produce a “bogus” lease in order to obtain financing?  

If you are using STR, REPS, or self rental with material participation to convert to active or nonpassive income, you do not have to do this if you have passive business invesment that produce passive income that will exceed the loss generated by depreciation.

He became a contractor, worked hard, and grew a successful business that produced a lot of money.

On finding an agent, you make a completely valid point about the top producing agents.

@Thomas Farrellmiscellaneous reactions-BRRRRs won't produce cash flow - they're an equity strategy, not a cash flow strategy-OOS BRRRR on your first deal will be incredibly difficult. 

But when it comes to choosing or creating investments that will produce a return along with personal fulfillment or enjoyment, then I say it definitely matters what you invest in and where you invest.  

To maximize your tax advantages, treat 75% of the property as rental income-producing, allowing you to deduct expenses like mortgage interest, property taxes, and depreciation on that portion.

I found a property in my area that would produce decent cash flow and appreciation; however, I would have to use funds from a HELOC on a different rental property for the down payment.

Hard to produce cash flow or break even with that much debt, at that rate.House-hackers, however enjoy certain one time (non-scalable) advantages that should be taken advantage of in the early days: - They can assume pre-existing debt like VA and FHA Loans (rather than take it on Subject-To which is dramatically riskier).- They can rent by the room and self-manage to produce day 1 cash flow.- Many of these HCOL areas also have strict limitations on AirBnB or short-term rentals... that do not apply to owner-occupants - thus allowing for extreme cashflow potential for house-hackers.

A and B neighborhoods typically don’t produce much cash flow and are more of an appreciation play—something the city has been seeing quite a bit of over the past decade.