I would also consider scaling back major expenses like car payments, lavish shopping, etc.

Also the Adelson family of Las Vegas Sands fame have purchased a couple of big parcels with hopes to build a giant casino/convention resort perhaps anchored by the arena for the Mavericks for which they also just purchased majority ownership from Mark Cuban. 

Even my seasoned and great landlords are going to have major issues with this.

fix and flips are the vast majority of the targets for private lenders.

Also the majority of those costs to covnert to a 2nd unit will need to be capitalized and depreciated, but some things (new appliances, flooring, paint, kitchen cabinets) can be shorter year assets vs. across the full 27.5 and IF it turns out that unit is > 50% you can use bonus as well on those items.

I suspect this would happen if various parties were given the ability to ask questions in nearly every application for what this thread touches on - and I have major concerns about integrity (and credibility) issues involved in putting yourself in a position to defend this position if ever challenged. 

It does feel like there is likely a major market correction coming, but due to limited inventory of vacation-rentable units in Maui I feel like I should be somewhat more protected from the effects of said recession.

And he can purchase the property himself from the defaulting borrower, or purchase a (majority) ownership in the subject property.  

If FNMA, FNMA allows transfer of deed to LLC if mortgage originated after June 1, 2016 and original borrower owns a majority interest in the LLC and any 12 months of owner-occupancy is first met:https://servicing-guide.fanniemae.com/THE-SERVICING-GUIDE/Part-D-Providing-Solutions-to-a-Borrower/Subpart-D1-Assisting-the-Borrower-with-Property-Related/Chapter-D1-4-Transfers-of-Ownership/Section-D1-4-1-Information-Relating-to-Transfers-of-Owner/D1-4-1-02-Allowable-Exemptions-Due-to-the-Type-of-Transfer/1041300841/D1-4-1-02-Allowable-Exemptions-Due-to-the-Type-of-Transfer-09-09-2020.htm

I'm a carpenter / contractor by trade, and I've done a few major whole-house renovations of personal homes over the last decade or so.