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

"I was looking at get my property rented by the room to college students or Veterans" but I don't actively see this happening often.

For example, they lost a fairly major battle when they tried to argue that only licensed professional can manage short term rental properties. 

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.

And i have seen other do it like i said in San Antonio only to have that operator get in major trouble with the state and the investors get wiped out.. there is more than just YOU buying a home without an investor putting up the dollars to buy it.

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.

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.  

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

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