If you have the flexibility at this point in your life to house hack you should definitely take it!

If you would be interested let’s connect I have a lender recommendation that would be able to fund this deal with flexible terms and quick closing.

Doing this like a brrrr I see as the best bet, for example my property does still have room for improvement adding a bedroom and bath to the primary structure and then the ADU.

It is meant to be general and flexible.

But the flexibility of your schedule, no boss or direct customers, and potential for a great year, and realistic expectation that you set make it all doable.   

Your standards can be even tighter based on bedroom size, flexible space, plumbing capacity, and other factors.Check out the Keating Memo from HUD to learn more: https://www.hud.gov/sites/documents/DOC_7780.PDF

The safest bet is to try to get a variance from Union City. though clever, your combined unit lease agreement would likely cause trouble if ever scrutinized by the Tenants or the municipality. 

I think the outskirts are you best bets!

Sure, private lenders can often be a great solution for overcoming these challenges since they offer: Flexible Terms: Private lenders are more flexible with loan terms compared to traditional banks.

Yeah - the way we view it is that we have a "net" hurdle we want to make on the loan, but are agnostic on whether that is earned on the backend or frontend or a mix of both - but to be transparent and flexible to give the borrowers all the options (up to them if they want a high rate / low or no points, low rate / high points, or mix)