But that assumption, implies that the rental property you are buying is actually negative cash flow, which is not what people are looking for (unless there is far larger appreciation component than you are giving credit for).  

I know they are larger, but they are a credit union.

Every deal I've been a part of had a lender that would have had this requirement, but those deals were all larger multifamily syndications.

Unless you have a deal in the works, need cash fast, have other debts, or have fears about the market a conventional cash-out ReFi is the optimal choice.

It is a great vehicle of investment for those that have busy successful careers but still want to partake in the benefits of investing in large real estate deals. 

Would airbnb'ing the casita or house be realistic and provide you a larger some of cash flow? 

If the equity is larger (because of appreciation and /or principal pay-down) additional buyer funds and / or a seller wrap-around mortgage (wrap) can be written.  

You have made the choice, now it is about finding your investment method.

I work with a lot of investors and they tend to gravitate to some local guys, but the choice is yours of course.  

If you are investing in a trucking business, that should return cash far exceeding your investment.I would personally go for larger cash out so you maximize cash out for the loan costs.