This is a real estate company that doesn't even hold these funds in real estate?

Then he admitted his biggest mistake was not holding properties, so I asked why.

We track that on a quarterly basis, as I think it is the best way to hold yourself accountable.

While your properties hold significant equity, adding debt from HELOCs or a DSCR loan could strain your finances if STR performance fluctuates or costs rise.

Sometimes they still have the garage door and drywalled the inside... meaning that they did not do a foundation on the garage door line : they did not use a deputy inspector, they did not use the appropriate hold downs (metals) for structural integrity, they did not use the right calculations for framing (ie rafters for ceilings ) that are often changed in a garage conversion... did not use proper headers for windows and doors... etc etc I have been faced with these a lot when representing the buyer and I would : 1.

What is holding you back from just jumping in and doing it?

I know some mentioned about developing banking relationships and I totally agree with that, so here is what you do. 1) Open a business checking account in the name of your LLC to hold the assets. 2) Deposit your cash into that account to fund the real estate purchases3) After owning for 60-90 days, talk with a local lender about a line of credit against the 2 properties at 60% LTV. 4) After about 30-45 days, have the line open to use if you need that liquidity that you used, but until then you are not paying 7% interest on nothing. 

Instead of focusing solely on cash flow after a large down payment, we analyze how the property performs with less cash in so you can see if it holds up.

In CA a third party, escrow agent, generally holds the EDM, but at times, the FSBO wants to hold the EDM or is unaware of how to hold the EDM.

If not, you will have to utilize hard money which will drastically increase holding costs.