Thing#2 - Use your owner occupant status to its full benefit (Low down payment-Lower interest rate, etc) and buy your next rental property now as an owner occupied home and live in it for a year or two while saving for rental property number three - Buy rental number three as an owner occupant and live in it for a year or two while saving for rental number four .... and so on.You see that your wife will need to be onboard for this to work out - You will be buying a home that is possibly not quite what she may have in mind for your "forever" home and there will be occasional moves as you acquire new investment properties - Eventually, you will not be able to continue this technique and you will get to buy that "forever" home.  

Are they still on board with you??

My investor is on board with this. 

Does anyone know a lender who will jump on board?

Allow time and frustration during your recruiting and onboarding phase.

I've got an attorney and lenders on board so far but the broker is, himself, the seller soooo not sure how typical that is.

Yeah negative equity is not good, and make sure that the lender is on board with 5% down for a non owner occupied investment property before assuming that they are. 

However, like you said, Its hard to get someone on board when you have no experience. 

He wants to retire so I'm planning to buy him out and keep my bil on board as a small percentage partner with no ownership. 

I am 100% on board with flipping and holding a property myself, even partnering, Refi'ing, and paying out if there's enough meat.