And again, with a separate parcel it should be easier to finance the construction and do a cash out refi. 

So the idea of doing this all from afar is a bit daunting, however, I know the most important thing here will be to create a great team and outsource as much as possible.I have set my sights on a couple of different markets being in the Southeast and the Midwest; these markets seem to provide the cash flow I am initially interested in generating to value add to the properties I purchase.

Cash invested: $18,000 Sale price: $32,000 '69 trailer fix and flipNew flooring in kitchenAdded ACNew windowsAdded GarageNew interior panelsBathroom reno What made you interested in investing in this type of deal?

What's the point of getting cash flow if you lose all your capital?

Purchase price: $375,000 Cash invested: $87,000 STR What made you interested in investing in this type of deal?

You will make more money on appreciation when you sell your property than you likely will from the monthly cash flow.  

Which one is more appealing - continuing to own the house or the security of that much cash/liquidity?

Low down payment AND it cash flows also AND buyer has title.Maybe I am asking too much, but I don't think so.Perhaps you just market to homeowners.

The accountant would record it as of Jan and not Dec. 90% of the real estate investors are running cash-basis.

Since you’re already networking and have some good realtor contacts, focus on narrowing down your investment strategy (like buy-and-hold or house hacking) and target markets with solid cash flow potential.