If they aren’t able to show liquidity then they are higher risk if they take on a large unplanned expense in the future.

The original Idea was to convert the storage unit into a J-ADU, but since we don’t plan on being here after the garage conversions are done, the owner occupancy requirement for JADU will not be satisfied.

From an investment property point of view most lenders will require 20-25% DP so the VA loan advantages only go so far. 0% down in this market is risky anyways.

Those areas typically require 30 day minimum and some areas you can rent out 3x maximum/yr.

Pretty much every lender I know requires some experience as a developer...even if you work for one now.

Just open a separate bank account, give it a business name and keep track of all income and expenses.

They also require less day-to-day management.

Here's a few online sources on the matter:The fact of the matter is, the landlord cannot “double-dip,” collecting full rent from one tenant, who has vacated, and collecting again from the new tenant.From: https://corealestateattorneys.com/breaking-a-colorado-residential-lease/In Colorado, landlords are usually required to mitigate damages if you move out of your rental before the lease is up.

I don't really expect the property to cash flow, I realize that it's an expensive place to operate a STR and that on-island management is necessary by Hawaii law, but I'd like to be able to cover most of my mortgage and expenses after putting 30-40% down.

It provides a lower cost of entry than a property in the city but not at the expense of much lower rent.