Ouch, that cuts. 

A multi-single member LLC in Wyoming seems a very odd choice unless you mean a Series, but that will still get each Child Series (as with all Series) subject to the $800 minimum a year Franchise Tax.The only irrevocable trust would be one for your Primary & secondary residence - but then it is expensive to break that, you have to figure out your life expectancy to anticipate the trust ending before the end of your life to get any tax advantages and the QPRT no longer has the incredible tax advantages it used to (though it might in 2026 when/if it reverts back to the old structure) since the sweeping changes of the Tax Cuts and Jobs Act (TCJA) in 2017. 

CLICK HERE for one source that includes a link to the real estate agency where you can get it straight from the horse's mouth.

Uncle Sam doesn't get a cut. 

You stated that the JADU can't be more than 50% of the primary residence which would put the JADU at 450sqft since the main property is just over 900Sqft.I think my main question is would I be able to go straight into a JADU add on that is attached to the main house with a max footprint of 450sqft?

What really cuts into your STVR profits is $400-600 monthly HOA.PM me if you need any recommendations for property managers in the area.

There isn't any specific lenders for an ADU however I know of companies which will fund and build an ADU but take a cut of your gross rent for a specific term.

I just don't want the cut end to be raw on the edge of the counter top

And, if you're not cut out for it, don't feel bad, tons of other investors aren't good at leasing either, and they use property management with good results.

isn't going to cut it; not b/c they don't talk to those sellers of beat up properties, but because they become the listing agent when they find those sellers, and see above for how listing agents feel about 203k) and/or c) the buyer has 10+ years of marketing and/or sales experience.