On the plus side, you can transition to a more flexible plan document by working with a plan provider who can restate the brokerage firm documents if you ever wanted to.

Ken,As a whole, military personnel tend to be flexible and make the best of all different types of living situations. 

Selling it and paying off our primary residence would be an emotional win, allow us to pocket more of our income ("virtual cash flow"), leave us a little extra cash to purchase another SFR or duplex investment property, and allow flexibility for potential job transitions in the future. 

***I have a flexible work schedule and get free unlimited airline tickets*** I do not want to buy in my home state of Massachusetts and am hoping to move sometime in the near future (but probably after buying).

However, the HELOC is far more flexible than a Cash-out Refi since it is reusable and you can pay it back with a cash flowing property lowering your overall payment on the HELOC.

But I can’t seem to convince her that with having someone help us pay the mortgage I could have the flexibility of taking some days off of work to spend more time with the family and not feel so tied to work.

Beside from protection, it will provide you with flexibility when it comes to taxation, management and ownership. 

I would be readily available  and extremely flexible to work when needed which I think is my most valuable asset.

These might be preferable to a Task Rabbit which may not specialize in showcasing your apartment nor be as flexible.

@Deniz EkerConstruction to perm loans are good for a few reasons:they're paid out in draws so you only pay on money borrowedthey fund the construction so you don't have tothere are some out there that only have one closing, saving you moneythey allow the flexibility of building on your lot, the builder's lot or purchasing the lot with the first drawyou control the draw so if a sub skips town before they're finished, they don't get paidback to one closing.