A good lender should be able to piece together a strategy with you, whether that's cross collateralizing or not, underwrite each option with conservative numbers. 

Quote from @Jimmy Chao: I am weighing some options to help my younger brother buying his first primary with a fixer.

(This option would would not carry any debt, all debt would be paid in cash)Or keep our current house, rent it out, and cash flow NET monthly about $1,500?

No syndication experience but there are about a dozen quality RV/Mobile home parks on market in Oregon, several with owner carry options that can be passiv-ish with management in place.

I figure if the equity we have cash flows better than similar equity in a single family residence in Utah would, then we should consider this AITD as a serious option.

I would go with option A.

The increasing barrier to entry results in fewer new STR's coming available for sale, but also fewer options for guests to rent. 

In addition to what was said above, for the software that has a free trial option, sign up for it and use the software for a day (or at least a few hours) as if you are using it for real, then call their customer support too and get a feel for that. 

I met with Wicked Smart today and was told they help you set up a lead sourcing system, help you structure creative financing - which is essentially lease option/purchase, subject to and owner financing....all strategies I am interested in learning more about.

Thank you,Jerry Jerry, I recommend getting in touch with an experienced broker who can educate you on all the possible options in the investment space for cash-out refinances.