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. 

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.

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.  

One of the lease for a rental is about to expire and would like to change from single family to rent by the room and try, to market for regular leasing we normally go to Zillow and advertise for free, but for rent by the room not sure which of all the sites out there will be the best option(s), some of them are for free, majority pay a monthly or anual subscription ($99 to $200).Do you have any guidance on which to select?

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

Technology is a good partner the more you know on your own.You should make a list of areas you might be interested in first - maybe you lived there or have friends there, you always wanted to go there - and then compare that list to some best areas list, do some of your own research, and then use a major data tool to look.

Franklinton is undergoing rapid transformation, with developments like The Gravity Projects, new breweries, and an expanding arts district driving change.Safety and Future Outlook:Increased Investments: New developments bring better lighting, public spaces, and infrastructure, naturally improving safety.Community Growth: More residents and businesses create activity, discouraging crime and boosting the neighborhood's vibrancy.Police and Outreach: Enhanced patrols and local organizations address crime and substance issues.While challenges remain, ongoing investments and gentrification make Franklinton safer and more attractive.

Population is growing and the job market is strong (major employers developing like Intel, Amazon, Meta, etc.)