For 379k and it cash flows.

If you prefer more liquidity, using cash flow to build savings may be a prudent choice.

MF houses provide improved cash flow, economies of scale, and faster portfolio development, but they may not appreciate as quickly.

You should be able to take into consideration if the property makes sense as a rental when you move out, will it cash flow then after a few years, or will part of your strategy be to fix up your side while you live there and then either move into the other side at some point to fix it up or to just sell when you’re ready to move to a different location if it doesn’t cash flow at that point.

Also, cash flow will be lower with a higher loan amount on a property. 

Don't borrow or cash out from the retirement account. 

Essentially, I want all cash flow/expenses to be flowing in and out of a business account rather than my personal bank accounts. 

Might be able to get a contract with the buyer of the cherries and thow some cash at you upfront for signing a agreement to buy the crop but I don't know what the alternate bearing looks like on Cherries in Washington and the brokers may not be willing to pay upfront in that area... or a upfront lease payment from the renter... 

The way I see it, a brand spanking new duplex wouldn't be the smartest deal because of the high purchase price and you'd likely not cash flow, if not be in the negative.

That $153k would allow me to buy 2-3 rentals and cash flow close to the same amount/ maybe a little more each month.