No, because a) that might be their luxury/vice item for all I know, which is 100% fine if it's viewed as a luxury item that they just really personally enjoy and gain happiness from (it's much less harmful than other vices, like drugs or gambling!)

I have chosen the move out path. 

Your add should seek a builder, with tools, who can build your chosen design, within 6 months. 

It's a little bit of a gamble for both of you, but I think a fair one. 

Hopefully during that time the house appreciates (always a gamble and never guaranteed). 

You can have a cash-flowing property that has a loss for tax purposes, primarily due to the effects of depreciation (a non-cash expense).If you have a negative cash flowing property, then your only financial benefit as an investor is the gamble on property appreciation.

I know I’m ignoring any appreciation, but I hear over and over again not to count on appreciation because that’s a gamble.

An ideal neighborhood within that market is one that offers the best of both worlds for appreciation and cash flow relative to the market you've chosen.

I’ve chosen an applicant and was working on creating an lease through rocket lawyer.

We are looking to gain as much knowledge and guidance as we can from such a staggering collection of professionals and mentors in our chosen area to build a more financially solid foundation for our future retirement.