The governments own estimates are that Social Security will be depleted by the year 2030-ish, now with Covid making a whole lot of folks filling for early retirement just to get some money coming in (money going out) and so many out of work (money not going in) depletion will probably be at the end of this decade smh.

I could technically quit my job and live off the profits from these 4 homes today but I am more risk averse than that and would like to have more cash reserves after they've been depleted a bit to acquire these homes.I'm always amazed how people are able to build a portfolio of 40, 50, 100 homes and haven't quite figured out how to do that unless most of those homes are under $100,000 (or much less) and they've been doing it 10+ years, but you do hear of it on the Bigger Pockets podcast.So, given all that:1) What am I doing right?

Next thing she knew, they were calling her to put more money into her reserve account that started out at $6,000 and was depleted in just a few months. 

In addition shale oil wells deplete significantly faster than traditional wells. 

While this can certainly be true Kim (debt to income can degrade) some key points I'd like to point out to people who might be considering conventional financing and getting loans :- you can use rental income with no landlord experience - Fannie Mae (Freddie Mac requires min 2 years on tax returns or CPA letter to state 2 years exp but most CPA's will not write that letter for you to protect their license)- you can add back depreciation and other non cash losses like depletion or amortization as these items are accounting losses and lenders are concerned with the "actual," cash flow that you will have available to service their loan they are thinking about extending to you- you can add back capital expenses as well if you can document it (make sure to save all receipts and invoices =D) since this tends to occur with investors the first year that complete many capital upgrades. since these are not normal occurrences every year they may be added back to improve your income if the file is structured correctly.- If a buyer buy's property that is still positive after the formula (gross monthly rent X 75% - PITIA) then you will actually improve your debt to income not hurt it contrary to what most think.

I am considering moving my IRA to a self-directed IRA and told a friend and he said he took the tax hit and depleted his IRA and is happy he did.

Definitely not wanting to deplete my savings..  

Or would it be better to pay it outright, depleting my savings, but getting a property that actually cash flows in todays market?

That's just it, though - the inventory is so depleted there's no way the higher prices make up for the lack of inventory.

Costs for rentals can quickly deplete any CF you have and the less dollars per door, the more risk you assume.