Talk to your accountant about gifting.

Could we use cash from a home equity loan on the property in MI to provide a down payment for a new place in HI, and if that could be used as a gift to us and allow us to use my husband's VA loan? 

And fortunately for the environment a lot of those people are millennials who want to walk to work, play and shopping, or, at least take public transportation.

Gift them a copy of BiggerPockets' book First to a Million, written specifically for Gen Z.https://store.biggerpockets.co...

You can't get gift from your sister for investment.

@Ibn Abney in both cases you mention, Oakland and NYC, both real estate markets were driven by the concentration of technology companies that came into the area with jobs, attracting the youth with better jobs.Chicago has............................. no technology companies wanting to set up shop there and the number one city in the US where people are leaving the area.Without technology companies wanting to set up shop in droves, it's a dying city in my opinion.  

I would be happy to grab lunch with you and talk shop, but I will be out of town this weekend for a wedding.

I am shopping for insurance and I'm a little sticker shocked.

@April Laspinas you’ll need to shop for other lenders.

Secondly, if going with the LLC ends up being the correct path for me, would I register that in my home state or the state the investment property is in (I live in MA and I am shopping in RI).Thank you!