To anyone considering such generational structure, I suggest: - Wyoming as a organization state.

This setup helps you stay organized, prepared for tax season, and ready for unexpected expenses.

These do require more time and organization though.Looking forward, after 5+ years of owning a property, assuming you bought in an appreciating area, you should have enough equity built up via tenants paying down your mortgage for you and appreciation to refinance out of the VA loan (if you haven't already) or even cashout to buy more or to supplement your earnings.Theoretically, if you have enough properties you could refinance at least one a year.

The PadSplit platform should be used as a resource/tool but please engage with the people in the organization.

I am working with a nonprofit organization that will be using this home for a program that is geared strictly to homeless veterans to find them suitable housing and assistance with finding jobs.

I love where you mind is at and how organized your post/plan is.

All the ingredients exist, it only needs organization and leadership. 

Meetups are typically organized by other investors and have invited guests to speak to their group.

Quote from @Zachary Deal: One thing to keep in mind if you are doing this is that you are likely to create "functional obsolescence" which could mean you are not able to get a new loan against your property and it can be difficult to resell as well. 

With permit, benefits are 1) get depreciation and other tax write off benefits since it’s a permitted investment purpose ADU, 2) probably better for resell value, 3) have a separate address and don’t have to bother sorting out mails for our legal tenant, etc. without permit; benefits are 1) no hassle to get the permit, 2) no permit fees, 3) no tax on rental income (as it is more like a “roommate”)Has anyone gone through a similar situation before?